Azo dyes from five membered ring heterocyclic amines and aniline, tetrahydroquinoline and benzomorpholine couplers containing thiosulfate alkyl groups

ABSTRACT

Disclosed are mono azo dyes derived from diazotized 5-membered heterocyclic amines and certain aniline, 1,2,3,4-tetrahydroquinoline, and benzomorpholine couplers containing thiosulfate alkyl groups. These dyes are useful for dyeing synthetic fibers, cellulose acetate and wool, and particularly impart fast violet to blue shades on polyamide fibers, and in general, exhibit improved properties such as fastness to light, sublimation, ozone, oxides of nitrogen, perspiration, crock, and wash, and exhibit excellent build, pH stability, bloom resistance, depth of shade, leveling, migration, and the like. The dyes have the general formula: 
     
         D--N═N--Coupler 
    
     wherein D is a thiadiazol, isothiazol, pyrazol or thiophene type radical, and the Coupler is an aniline, tetrahydroquinoline, or benzomorpholine derivative wherein a --ZSSO 3  M group is attached to the nitrogen thereof, the coupler ring may contain substituents such as alkyl, alkoxy, halogen, acylamido, alkylthio or aryloxy, the remaining hydrogen of the aniline coupler may be replaced by a substituent such as alkyl, substituted alkyl, alkenyl, aryl, or cycloalkyl, M is Na + , K + , NH 4   +  or H + , and Z is a linking group such as ethylene.

This invention concerns mono azo dyes derived from diazotized 5-membered heterocyclic amines and certain aniline, 1,2,3,4-tetrahydroquinoline, and benzomorpholine couplers containing thiosulfate alkyl groups. These dyes are useful for dyeing synthetic fibers, cellulose acetate and wool, and particularly impart fast violet to blue shades on polyamide fibers. The dyes, in general, exhibit improved properties such as fastness to light, sublimation, ozone, oxides of nitrogen, perspiration, crock, and wash, and exhibit excellent build, pH stability, bloom resistance, depth of shade, leveling, migration, and the like.

The dyes of this invention have the general formula:

    D--N═N--Coupler

wherein D is a thiadiazol, isothiazol, pyrazol or thiophene type radical, and the Coupler is an aniline, tetrahydroquinoline, or benzomorpholine derivative wherein a --ZSSO₃ M group is attached to the nitrogen thereof, the coupler ring may contain substituents such as alkyl, alkoxy, halogen, acylamido, alkylthio or aryloxy, the remaining hydrogen of the aniline coupler may be replaced by a substituent such as alkyl, substituted alkyl, alkenyl, aryl, or cycloalkyl, M is Na⁺, K⁺, NH₄ ⁺ or H⁺, and Z is a linking group such as ethylene.

More specifically, the Coupler is of the formulae ##STR1## wherein R₁ is selected from hydrogen; alkyl; halogen; alkoxy; aryloxy; --NHCO--R₅ ; --NHSO₂ --R₅ ; wherein R₅ is selected from alkyl which may be substituted with hydroxy, alkoxy, cyano, aryloxy, aryl, halogen, cycloalkyl, alkylcarbonyloxy, or carbamoyl; aryl; alkylamino; and 2-furyl; R₂ is selected from hydrogen; aryl; cycloalkyl; and alkyl which may be substituted with alkoxy, alkoxyalkoxy, hydrogen, aryloxy, aryl, cycloalkyl, alkylcycloalkyl, furyl, acylamido, aryloxy, carbamoyl, alkoxycarbamoyl, alkyl substituted carbamoyl, cyano, alkanoyloxy, halogen, alkoxycarbonyl, succinimido, glutarimido, phthalimido, 2-pyrrolidono, sulfamoyl, alkyl substituted sulfamoyl, alkylsulfonamido, NHSO₂ -aryl, NHCOO-alkyl, NHCONH-alkyl, formamido, alkylsulfonyl, arylsulfonyl, alkylthio, arylthio or SO₃ M; n is 0, 1 or 2; M is Na⁺, K⁺, NH₄ ⁺, or H⁺ ; R₃ and R₄ are each selected from hydrogen or alkyl; Z is selected from straight or branched chain alkylene; alkylene substituted with aryl, aryloxy, alkoxy, halogen, aryloxy or SO₃ M; --CH₂ (CH₂)_(m) --X--CH₂ (CH₂)_(p), where m is 1, 2, or 3, p is 0, 1, 2 or 3, and X is O, S, SO₂, --SO₂ NH--, ##STR2## the various aryl groups above may be substituted with alkyl, alkoxy, or halogen; and each of the above alkyl, alkylene, alkoxy, alkenyl and the like moieties contain from 1-6 carbons.

The heterocycle D is of the formulae ##STR3## wherein

ring A may bear a substituent selected from alkyl, substituted alkyl, alkoxy, halogen, alkylsulfonyl, SO₂ -aryl, SO₂ NH₂, SO₂ NH-alkyl, SO₂ N-(di-alkyl), substituted SO₂ NH-alkyl, acylamido, aryl, arylthio, alkenylthio, cyclohexylthio, thiocyano, cyclohexylsulfonyl, alkylthio, substituted alkylthio and cyclohexyl;

ring B may bear a substituent selected from alkyl, substituted alkyl, aryl, alkylthio, cyclohexylthio, substituted alkylthio and alkylsulfonyl;

ring B may bear a substituent selected from alkyl, substituted alkyl, aryl, alkylthio, cyclohexylthio, substituted alkylthio and alkylsulfonyl;

ring C may bear one or two substituents selected from alkyl, substituted alkyl, halogen, cyano, carbamoyl, CONH-alkyl, substituted CONH-alkyl, alkoxycarbonyl, alkylthio, substituted alkylthio, alkenylthio, arylthio, cyclohexylthio, S-heterocycle, aryloxy, and alkoxy;

ring D may bear one or two substituents selected from alkyl, substituted alkyl, alkoxycarbonyl, alkylthio, aryl, cyano, carbamoyl, alkyl carbamoyl, alkylcarbonyl, substituted alkyl carbamoyl, and alkyl sulfonyl; and the A group on the 1-nitrogen of ring D may be hydrogen, alkyl, alkoxycarbonyl, aryl, alkylsulfonyl, arylsulfonyl, or alkanoyl;

ring E may be substituted with one to three substituents selected from alkyl, substituted alkyl, cyano, alkoxycarbonyl, acyl, aroyl, alkylsulfonyl, arylsulfonyl, carbamoyl, alkyl carbamoyl, substituted alkyl carbamoyl, aryl, halogen, sulfamoyl, substituted alkyl, and formyl;

wherein the various alkyl, alkylene, alkoxy and other such moieties contain from 1-6 carbons and may bear one to three substituents selected from hydroxy, halogen, alkoxy, aryl, aryloxy, cyclohexyl, alkylcyclohexyl, acyloxy, alkoxy carbonyl, acylamido, alkylsulfonamido, succinimido, glutarimido, phthalimido, 2-pyrrolidono, cyano, carbamoyl, alkoxy-alkoxy, alkylthio, halogen, arylthio, alkylsulfonyl and arylsulfonyl;

and wherein the various aryl groups may be substituted with one to three substituents selected from alkyl, alkoxy, halogen, alkoxy carbonyl, alkyl sulfonyl, and alkylthio.

The following couplers are particularly valuable in the practice of this invention. ##STR4## The couplers of this invention are prepared by reacting N-chloro (or bromo) alkyl aromatic amines with an alkali thiosulfate salt.

The following coupler intermediates are typical of those appropriate for reacting with sodium thiosulfate. ##STR5##

The halogen containing couplers are in general prepared by reacting the corresponding known hydroxy compounds with POCl₃, SOCl₂, POBr₃, PBr₃, and the like by methods well known in the art. The tetrahydroquinoline and benzomorpholine intermediates are similarly prepared.

This invention will be further illustrated by the following examples although it will be understood that these examples are included merely for purposes of illustration and are not intended to limit the scope of the invention.

Preparation of Typical Couplers EXAMPLE 1 Sodium S-2-[ethyl(3-methylphenyl)amino] ethyl thiosulfate

Sodium thiosulfate (49.6 g, 0.2 m), sodium iodide (1 g), N-2-chloroethyl-N-ethyl-m-toluidine (19.8 g, 0.1 m), and 200 ml water were mixed and heated at about 95° C. for about 11/2 hrs. The reaction mixture was cooled to about 20° C. and filtered. The white solid was washed with hexane and dried in air. Yield--26.0 g (87.5%).

EXAMPLE 2 Sodium S-2-(1,2,3,4-tetrahydro-2,2,4,7-tetramethyl-1-quinolinyl)ethyl thiosulfate

A mixture of sodium thiosulfate (49.6 g, 0.2 m), sodium iodide (1 g), N-(2-chloroethyl)-2,2,4,7-tetramethyl-1,2,3,4-tetrahydroquinoline (25.2 g, 0.1 m), water (100 ml), and ethanol (100 ml) was refluxed fro 3 hrs. The mixture was cooled and extracted with 2-75 ml portions of toluene. The aqueous layer then contained essentially pure product and aliquots were used to prepare dyes without further purification.

EXAMPLE 3 Sodium S-2(3,4-dihydro-3,6-dimethyl-2H-1,4-benzoxazin-4-yl)ethyl thiosulfate

Sodium thiosulfate (0.2 m), sodium iodide (1 g), N-(2-chloroethyl)-3,6-dimethyl-2H-1,4-benzoxazine, water (150 ml), and ethanol (75 ml) were mixed and heated at reflux for 3 hrs. The alcohol was distilled off and the reaction mixture was cooled. The product, a white solid, was collected by filtration and dried in air. The yield was essentially quantitative. Preparation of the Dyes

EXAMPLES 4-8 Diazotization and Coupling of 2-Amino-5-ethylthio-1,3,4-thiadiazole

Sodium nitrite (3.6 g.) is added portionwise to 25 ml of concentrated H₂ SO₄. The solution is cooled and 100 ml of 1:5 acid (1 part propionic :1 part acetic) is added below 15° C. The mixture is cooled and 8.05 g. (0.05 m) of 2-amino-5-ethylthio-1,3,4-thiadiazole is added below 10° C. After stirring at 0°-5° C. for 2 hrs., a 0.005 m aliquot of the diazonium salts is added to 0.005 m of the following couplers in water or dilute sulfuric acid, keeping the temperature below 5° C.

EXAMPLE 4 Sodium S-2[ethyl(3-methylphenyl)amino]ethyl thiosulfate EXAMPLE 5 Sodium S-2[ethyl(phenyl)amino]ethyl thiosulfate EXAMPLE 6 Sodium S-2-(1,2,3,4-tetrahydro-2,2,4,7-tetramethyl-1-quinolinyl)ethyl thiosulfate EXAMPLE 7 Sodium S-2-(2,7-dimethyl-1,2,3,4-tetrahydro-1-quinolin yl)ethyl thiosulfate EXAMPLE 8 Sodium S-2-(3,4-dihydro-3,6-dimethyl-2H-1,4-benzoxazin-4-yl)ethyl thiosulfate

The mineral acid is neutralized with sodium acetate and the coupling mixture allowed to stand for 1 hr. Water is added to make a total volume of 200-300 ml. and the dyes are collected by filtration, washed with water, and dried in air.

The dyes usually contain about an equal weight of dye and sodium sulfate as they are isolated and are used for dying polyamide fibers red shades without further purification.

EXAMPLES 9-13 Diazotization of 5-Amino-3-ethylthio-1,2,4-thiadiazole

5-Amino-3-ethylthio-1,2,4-thiadiazole (8.05 g., 0.05 m) is diazotized exactly as described in Examples 4-8 and a 0.005 m aliquot coupled to 0.005 m portion of the couplers of Examples 4-8 in the manner previously illustrated.

EXAMPLES 14-18 Diazotization of 5-Amino-3-methyl-4-cyano isothiazole

To 25 ml of concentrated H₂ SO₄ is added 3.6 g. of NaNO₂ allowing the temperature to rise. The solution is cooled and 50 ml of 1:5 acid is added below 10° C. Stirring is continued and 6.95 g. (0.05 m) of 5-amino-3-methyl-4-cyanoisothiazole is added below 5° C., followed by an additional 50 ml of 1:5 acid. After stirring at 0°-5° C. for 2 hrs., a 0.005 m aliquot of the diazoniu m salt is coupled to 0.005 m of the couplers of Examples 4-8 as previously described to produce rubine to violet dyes for polyamides.

EXAMPLES 19-23 Diazotization of 5-Amino-4-carbomethoxypyrazole

Nitrosyl sulfuric acid is prepared by adding 3.6 g. NaNO₂ to 25 ml of concentrated H₂ SO₄. The solution is cooled and 100 ml of 1;5 acid is below 20° C. After further cooling, 5-amino-4-carbomethoxypyrazole (7.05 g., 0.05 m) is added at 0°-5° C. and stirring continued for 2 hrs. A 0.005 m aliquot of the diazonium solution is coupled to 0.005 m. of the couplers of Examples 4-8 in the manner previously described to produce red dyes for polyamides.

EXAMPLES 24-28 Diazotization of 2-Amino-3-carbomethoxy-5-isobutyrylthiophene

To 150 g. of 60% aqueous acetic acid is added 11.35 g. (0.05 m) of 2-amino-3-carbomethoxy-5-isobutyrylthiophene at room temperature. Ten grams of concentrated H₂ SO₄ is added and the mixture cooled to 0° C. A solution of 3.6 g NaNO₂ in 25 ml of conc. H₂ SO₄ is added below 10° C. and stirring continued for 1 hr. at 0°-5° C. A 0.005 m aliquot of this diazonium salt is coupled to 0.005 m portions of the couplers of Examples 4-8 as previously illustrated to produce violet to reddish-blue dyes for polyamides.

The following tables of dyes will further illustrate the invention.

                                      TABLE 1                                      __________________________________________________________________________      ##STR6##                                                                      R            (R.sub.1).sub.m                                                                            R.sub.2        Z                  M                   __________________________________________________________________________     5-CH.sub.3   2-CH.sub.3  H              CH.sub.2 CH.sub.2  K.sup.+             5-CH.sub.2 CH.sub.3                                                                         2-Cl        "              "                  "                   5-CH.sub.2 CH(CH.sub.3)                                                                     2,5-di-Cl   "              "                  "                   5-C.sub.6 H.sub.5                                                                           2,5-di-CH.sub.3                                                                            "              "                  "                   5-C.sub.6 H.sub.11                                                                          2,5-di-OCH.sub.3                                                                           "              "                  "                   5-C.sub.6 H.sub.4p-Cl                                                                       3-OCH.sub.3 C.sub.2 H.sub.5                                                                               "                  "                   5-C.sub.6 H.sub.4o-CH.sub.3                                                                 2-OCH.sub.3, 5-NHCOCH.sub.3                                                                H              "                  "                   5-C.sub.6 H.sub.4m-OCH.sub.3                                                                2-CH.sub.3, 3-Cl                                                                           "              "                  "                   5-SCH.sub.3  2-OCH.sub.3 , 5-Cl                                                                         "              "                  "                   "            3-NHCOCH.sub.3                                                                             C.sub.2 H.sub.5                                                                               "                  "                   "            3-NHCOC.sub.2 H.sub.5                                                                      C.sub.2 H.sub.4 OCH.sub.3                                                                     "                  "                   "            3-NHCOCH.sub.2 OH                                                                          CH.sub.2 C.sub.6 H.sub.5                                                                      "                  "                   "            3-NHCOCH.sub.2 OCH.sub.3                                                                   C.sub.6 H.sub.11                                                                              "                  "                   H            3-NHCOC.sub.6 H.sub.5                                                                      CH.sub.2 C.sub.6 H.sub.11                                                                     "                  "                   "            3-NHCOOC.sub.2 H.sub.5                                                                     CH.sub.2 CH.sub.2 OC.sub.6 H.sub.5                                                            "                  "                   "            3-NHCONHC.sub.2 H.sub.5                                                                    CH.sub.2 CH.sub.2 OH                                                                          "                  "                   5-OC.sub.2 H.sub.5                                                                          3-NHCOC.sub.6 H.sub.11                                                                     CH.sub.2 CH(CH.sub.3).sub.2                                                                   "                  "                   5-SC.sub.2 H.sub.5                                                                          3-NHCOCH.sub.2 CN                                                                          CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                           "                  "                   "            3-NHCOCH.sub.2 OC.sub.6 H.sub.5                                                            CH.sub.2 CH.sub.2 OCOCH.sub.3                                                                 "                  "                   "            3-NHCOCH.sub.2 C.sub.6 H.sub.5                                                             CH.sub.2 CH.sub.2 CONH.sub.2                                                                  "                  "                   "            3-CH.sub. 3 CH.sub.2 CH.sub.2 NHCOCH.sub.3                                                                "                  "                   "            "           CH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.3                                                         "                  "                   "            "           CH.sub.2 CH.sub.2 SO.sub.2 NH.sub.2                                                           "                  "                   "            "           CH.sub.2 CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.3                                                  "                  "                   5-Cl         "           CH.sub.2 CH.sub.2 SCH.sub.3                                                                   "                  "                   5-SO.sub.2 CH.sub.3                                                                         H                                                                                           ##STR7##      CH.sub.2 CH.sub.2 CH.sub.2                                                                        Na.sup.+            5-OC.sub.4 H.sub.9n                                                                         "                                                                                           ##STR8##      "                  "                   5-SCH.sub.2 CH.sub.2 OH                                                                     3-OC.sub.6 H.sub.5                                                                          ##STR9##      "                  NH.sub.4.sup.+                                                                 4                   5-SCH.sub.2 CH.sub.2 COOCH.sub.3                                                            3-CH.sub.3  C.sub.6 H.sub.5                                                                               CH.sub.2 CH.sub.2  Na.sup.+             ##STR10##   "                                                                                           ##STR11##     CH.sub.2 CH(CH.sub.2 OC.sub.6                                                  H.sub.5)           "                   5-SCH.sub.2 SC.sub.6 H.sub.5                                                                "           CH.sub.2 CH.sub.2 COOCH.sub.3                                                                 CH.sub.2 CH(C.sub.6 H.sub.5)                                                                      "                   5-SO.sub.2 CH.sub.3                                                                         "           CH.sub.2 CH.sub.2 CN                                                                          CH.sub.2 CH(CH.sub.3)                                                                             "                   5-SO.sub.2 NH.sub.2                                                                         "           C.sub.2 H.sub.5                                                                               CH.sub.2 CH(OH)CH.sub.2                                                                           "                   5-SO.sub.2 NHC.sub.2 H.sub.5                                                                2-CH.sub.3 S                                                                               H              CH.sub.2 CH.sub.2 CH.sub.2                                                     CH.sub.2           "                   5-SCN        3-CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OC.sub.2                                      H.sub.5        CH.sub.2 CH(OCOCH.sub.3)CH.sub.2                                                                  "                   5-SO.sub.2 N(CH.sub.3).sub.2                                                                "           CH.sub.2 CH(OH)CH.sub.2 Cl                                                                    CH.sub.2 CH.sub. 2 "                   5-SO.sub.3 C.sub.6 H.sub.5                                                                  2-OCH.sub.3, 5-CH.sub.3                                                                    C.sub.2 H.sub.5                                                                               "                  "                   5-SCH.sub.2 CHCH.sub.2                                                                      "           H              CH.sub.2 CH.sub.2 OCH.sub.2                                                    CH.sub.2           "                   5-SCH.sub.2 CH.sub.2 OCH.sub.3                                                              "           H              "                  "                    ##STR12##   "           "              CH.sub.2 CH.sub.2 SO.sub.2                                                     CH.sub.2 CH.sub.2  K.sup.+             5-SC.sub.6 H.sub.11                                                                         3-CH.sub.3  C.sub.2 H.sub.5                                                                               CH.sub.2 CH.sub.2 SCH.sub.2                                                    CH.sub.2           "                   5-SC.sub.6 H.sub.5                                                                          "           "              CH.sub.2 CH.sub.2 N(SO.sub.2                                                   CH.sub.3)CH.sub.2 CH.sub.2                                                                        "                   5-SO.sub.2 C.sub.6 H.sub.5                                                                  "           "              CH.sub.2 CH.sub.2 NHSO.sub.2                                                   CH.sub.2 CH.sub.2 CH.sub.2                                                     CH.sub.2           "                   5-I          "           "              CH.sub.2 CH.sub.2 SO.sub.2                                                     NHCH.sub.2 CH.sub.2                                                                               "                   5-Br         "           "              CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.                                             sub.2 CH.sub.2     "                    ##STR13##   "           "              CH.sub.2 CH.sub.2 CONHC.sub.2                                                  H.sub.4            "                   5-SCH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.3                                                    "           "              CH.sub.2 CH.sub.2 NHCOCH.sub.2                                                                    "                   5-SCH.sub.2 CH.sub.2 NHCOCH.sub.3                                                           "           "              CH.sub.2 CH.sub.2 N(SO.sub.2                                                   C.sub.6 H.sub.5)CH.sub.2 CH.sub.2                                                                 "                   5-SCH.sub.2 CH.sub.2 OC.sub.6 H.sub.5                                                       "           "              CH.sub.2 CH.sub.2 SO.sub.2                                                     N(CH.sub.3)CH.sub.2 CH.sub.2                                                                      "                   5-SCH.sub.2 CH.sub.2 C.sub.6 H.sub.5                                                        "           "              CH.sub.2 CH.sub.2 SO.sub.2                                                     N(C.sub.6 H.sub.5)CH.sub.2                                                     CH.sub.2           "                   5-SCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                       "           "              CH.sub.2 CH.sub.2 N(SO.sub.2                                                   C.sub.6 H.sub.11)CH.sub.2                                                                         "H.sub.2            5-SO.sub.2 C.sub.6 H.sub.11                                                                 "           "              CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.                                             sub.2 CH.sub. 2    "                   5-CH.sub.3   "           "              CH.sub.2 CH(CH.sub.2 OCH.sub.3)                                                                   "                   "            "           "              CH.sub.2 CH(Cl)CH.sub.2                                                                           "                   "            "           "              CH.sub.2 CH.sub.2 NHCONHC.sub.2                                                H.sub.4            "                   5-NHCOCH.sub.3                                                                              "           "              CH.sub.2 CH.sub.2 NHCOOCH.sub.2                                                CH.sub.2           "                   "            "           "              CH.sub.2 CH.sub.2 COOCH.sub.2                                                  CH.sub.2           "                   __________________________________________________________________________

                                      TABLE 2                                      __________________________________________________________________________      ##STR14##                                                                     R             (R.sub.1)m     R.sub.3                                                                            R.sub.4                                                                               Z                  M                   __________________________________________________________________________     H             H              CH.sub.3                                                                           CH.sub.3                                                                              CH.sub.2 CH.sub.2  K.sup.+             "             7-CH.sub.3     "   "      "                  "                   "             7-OCH.sub.3    "   "      "                  "                   5-CH.sub.3    7-Cl           "   "      "                  "                   5-CH.sub.2 CH.sub.3                                                                          5-CH.sub.3, 8-OCH.sub.3                                                                       "   "      "                  "                   5-CH(CH.sub.3).sub.2                                                                         5,8-di-OCH.sub.3                                                                              "   "      "                  "                   5-CH.sub.2 CH(CH.sub.3).sub.2                                                                5,8-di-CH.sub.3                                                                               "   "      "                  "                   5-C.sub.6 H.sub.5                                                                            5-Cl, 8-OCH.sub.3                                                                             "   "      "                  "                   5-C.sub.6 H.sub.11                                                                           8-OCH.sub.3    "   "      "                  "                   5-C.sub.6 H.sub.4o-Cl                                                                        8-OC.sub.2 H.sub.5                                                                            H   H      "                  "                   5-C.sub.6 H.sub.4n-CH.sub.3                                                                  7-CH.sub.3     "   "      "                  "                   5-C.sub.6 H.sub.4p-OCH.sub.3                                                                 7-NHCOCH.sub.3 CH.sub.3                                                                           CH.sub.3                                                                              "                  Na.sup.+            5-OC.sub.2 H.sub.5                                                                           7-NHCOH        "   "      "                  "                   "             7-NHCOCH.sub.2 OCH.sub.3                                                                      "   "      "                  "                   "             7-NHCOCH.sub.2 OC.sub.6 H.sub.5                                                               H   CH(CH.sub.3).sub.2                                                                    "                  "                   "             7-NHCOCH.sub.2 C.sub.6 H.sub.5                                                                "   "      "                  "                   "             7-NHCOCH.sub.2 Cl                                                                             "   "      "                  "                   "             7-NHCOC.sub.6 H.sub.5                                                                         "   "      "                  "                   "             7-NHCOC.sub.6 H.sub.11                                                                        CH.sub.3                                                                           CH.sub.3                                                                              "                  "                   5-Cl          7-NHCONHC.sub.2 H.sub.5                                                                       "   "      "                  "                   "             7-NHSO.sub. 2 CH.sub.3                                                                        "   "      "                  "                   "             7-NHCOCH.sub.2 CN                                                                             "   "      "                  "                   "             7-NHCOCH.sub.2 OH                                                                             "   "      "                  "                   5-I           7-NHCOOC.sub.2 H.sub.5                                                                        "   "      CH.sub.2 CH.sub.2 CH.sub.2                                                                        "                   5-Br                                                                                          ##STR15##     "   "      "                  "                   5-SO.sub.2 CH.sub.3                                                                          8-OC.sub.4 H.sub.9n                                                                           H   CH.sub.3                                                                              CH.sub.2 CH.sub.2  "                   5-SO.sub.2 NH.sub.2                                                                          7-CH.sub.3     CH.sub.3                                                                           H      "                  "                   5-SO.sub.2 N(CH.sub.3).sub.2                                                                  ##STR16##     "   CH.sub.3                                                                              "                  "                   5-SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                                          7-OC.sub.2 H.sub.5                                                                            "   "      "                  "                   8-SO.sub.2 NHC.sub.3 H.sub.6 OCH.sub.3                                                       7-OC.sub.4 H.sub.9n                                                                           "   "      "                  "                   5-SO.sub.2 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                7-CH.sub.3     "   H      "                  "                   5-SC.sub.6 H.sub.5                                                                           "              "   "      "                  "                   5-SC.sub.6 H.sub.11                                                                          "              "   "      CH.sub.2 CH.sub.2 CH.sub.2                                                     CH.sub.2           "                   5-SO.sub.2 C.sub.6 H.sub.5                                                                   "              "   "      CH.sub.2 CH.sub.2  "                   5-SO.sub.3 C.sub.6 H.sub.5                                                                   "              "   "      "                  "                   5-SCH.sub.2 CH.sub.2 OH                                                                      "              "   "      "                  "                   5-SCH.sub.2 CHCH.sub.3                                                                       "              "   "      CH.sub.2 CH.sub.2 SO.sub.2                                                     CH.sub.2 CH.sub.2  K.sup.+             5-SCH.sub.2 COOC.sub.2 H.sub.5                                                               "              "   "      CH.sub.2 CH.sub.2 OCH.sub.2                                                    CH.sub.2           "                   5-SCH.sub.2 C.sub.6 H.sub.5                                                                  "              "   "      CH.sub.2 CH.sub.2 SCH.sub.2                                                    CH.sub.2           "                   5-SCH.sub.2 C.sub.6 H.sub.11                                                                 "              "   "      CH.sub.2 CH(C.sub.6 H.sub.5)                                                                      "                   5-SCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                        "              "   "      CH.sub. 2 CH(CH.sub.3)                                                                            "                   5-SCN         "              "   "      CH.sub.2 CH(OH)CH.sub.2                                                                           "                   5-SCH.sub.2 CH.sub.2 NHCOCH.sub.3                                                            "              "   "      CH.sub.2 CH(Cl)CH.sub.2                                                                           "                    ##STR17##    "              "   "      CH.sub.2 CH(CH.sub.2 OCH.sub.2                                                 CH.sub.3)          "                   5-SCH.sub.2 CH.sub.2 OC.sub.6 H.sub.5                                                        "              "   "      CH.sub.2 CH(CH.sub.2 OC.sub.6                                                  H.sub.5)           "                   5-SCH.sub.2 CH.sub.3                                                                         "              "   "      CH.sub.2 CH.sub.2 N(SO.sub.2                                                   CH.sub.3)CH.sub.2 CH.sub.2                                                                        "                   "             "              "   "      CH.sub.2 CH.sub.2 CH.sub.2                                                     NHSO.sub.2 CH.sub.2 CH.sub.2                                                                      "                   "             "              "   "      CH.sub.2 CH.sub.2 SO.sub.2                                                     NHCH.sub.2 CH.sub.2                                                                               "                   "             "              "   "      CH.sub.2 CH.sub.2 NHCOCH.sub.2                                                                    "                   "             "              "   "      CH.sub.2 CH.sub.2 NHCOOCH.sub.2                                                CH.sub.2           "                   "             "              "   "      CH.sub.2 CH.sub.2 COOCH.sub.2                                                  CH.sub.2           "                   "             "              "   "      CH.sub.2 CH.sub.2 CONHC.sub.2                                                  H.sub.4            "                   5-SCH.sub.3   "              "   "      CH.sub.2 CH.sub.2 NHCONHC.sub.2                                                H.sub.4            "                   "             "              "   "      CH.sub.2 CH.sub.2 N(SO.sub.2                                                   C.sub.6 H.sub.5)CH.sub.2 CH.sub.2                                                                 "                   "             "              "   "      CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.                                             sub.2 CH.sub.2     "                   "             "              "   "      CH.sub.2 CH.sub.2 SO.sub.2                                                     N(C.sub.6 H.sub.5)CH.sub.2                                                     CH.sub.2           "                   5-NHCOCH.sub.3                                                                               "              "   "      CH.sub.2 CH.sub.2 SO.sub.2                                                     N(CH.sub.3)CH.sub.2 CH.sub.2                                                                      "                   __________________________________________________________________________

                                      TABLE 3                                      __________________________________________________________________________      ##STR18##                                                                     R            (R.sub.1)m    R.sub.3                                                                           Z                     M                          __________________________________________________________________________     H            6-CH.sub.3    H  CH.sub.2 CH.sub.2     K.sup.+                    "            H             H  "                     "                          "            "             CH.sub.3                                                                          "                     "                          5-CH.sub.3   6-CH.sub.3    "  "                     "                          5-CH(CH.sub.3).sub.2                                                                        "             "  CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                                                  "                          5-CH.sub.2 CH(CH.sub.3).sub.2                                                               6-OCH.sub.3   "  "                     "                          5-C.sub.6 H.sub.5                                                                           "             "  CH.sub.2 CH.sub.2     "                          5-C.sub.6 H.sub.4p-Cl                                                                       6-CH.sub.3    "  CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2                                                                 "                          5-C.sub.6 H.sub.4p-OCH.sub.3                                                                "             "  CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2                                                                  "H.sub.2                   5-C.sub.6 H.sub.4n-CH.sub.3                                                                 "             "  CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.2                                                                 "                          5-OC.sub.2 H.sub.5                                                                          "             "  CH.sub.2 CH(CH.sub.3) "                          5-OCH(CH.sub.3).sub.2                                                                       "             "  CH.sub.2 CH(C.sub.6 H.sub.5)                                                                         "                          5-C.sub.6 H.sub.11                                                                          6-OC.sub.2 H.sub.5                                                                           "  CH.sub.2 CH.sub.2     "                          5-SCN        6-NHCOCH.sub.3                                                                               "  "                     Na.sup.+                   5-SCH.sub.3  6-NHCOH       "  "                     "                          5-SCH.sub.2 CH(CH.sub.3).sub.2                                                              6-NHCOCH.sub.2 CH.sub.2 OCH.sub.3                                                            "  "                     "                          5-SCH.sub.2 CHCH.sub.2                                                                      6-NHCOCH.sub.2 Cl                                                                            "  "                     "                          5-SC.sub.6 H.sub.11                                                                         6-NHCOCH.sub.2 CN                                                                            "  "                     "                          5-SC.sub.6 H.sub.5                                                                          6-NHCOCH.sub.2 CONH.sub.2                                                                    "  "                     "                          5-SCH.sub.2 C.sub.6 H.sub.5                                                                 6-NHCOCH.sub.2 OC.sub.6 H.sub.5                                                              "  "                     "                          5-SCH.sub.2 CH.sub.2 OC.sub.6 H.sub.5                                                       6-NHCOOC.sub.2 H.sub.5                                                                       "  "                     "                          5-SCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                       6-NHCONHC.sub.2 H.sub.5                                                                      "  "                     "                          5-SCH.sub.2 CH.sub.2 OH                                                                     6-NHCOC.sub.6 H.sub.5                                                                        "  "                     "                          5-SCH.sub.2 CH.sub.2 Cl                                                                     6-NHCOC.sub.6 H.sub.11                                                                       "  "                     "                          5-SCH.sub.2 COOC.sub.2 H.sub.5                                                              6-NHSO.sub.2 CH.sub.3                                                                        "  "                     "                          5-SCH.sub.2 CH.sub.2 OCOCH.sub.3                                                            6-NHCOCH.sub.2 CH.sub.2 OCOCH.sub.3                                                          "  "                     "                          5-SCH.sub.2 C.sub.6 H.sub.11                                                                 ##STR19##    "  "                     "                          5-SO.sub.2 CH.sub.3                                                                         6-NHCOCH.sub.2 CH.sub.2 CH.sub.2 OH                                                          "  "                     "                          5-SO.sub.2 C.sub.4 H.sub.9n                                                                 6-CH.sub.3    "  CH.sub.2 CH.sub.2 CH.sub.2                                                                           "                          5-SO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                      "             "  CH.sub.2 CH.sub.2     "                          5-SO.sub.2 C.sub.6 H.sub.5                                                                  "             "  "                     "                          5-SO.sub.2 C.sub.6 H.sub.11                                                                 "             "  "                     "                          5-SO.sub.2 CH.sub.2 C.sub.6 H.sub.5                                                         "             "  "                     "                          5-SO.sub.2 CH.sub.2 CH.sub.2 OH                                                             "             "  "                     "                           ##STR20##   "             "  "                     "                          5-SCH.sub.2 CH.sub.2 NHCOCH.sub.3                                                           "             "  "                     "                           ##STR21##   "             H  CH.sub.2 CH(CH.sub.3) "                          5-SO.sub.2 NH.sub.2                                                                         "             CH.sub.3                                                                          CH.sub.2 CH.sub.2 N(SO.sub.2 CH.sub.3)CH.sub                                   .2 CH.sub.2           K.sup.+                    5-SO.sub.2 NHC.sub.3 H.sub.6 OCH.sub.3                                                      "             "  CH.sub.2 CH.sub.2 SO.sub.2 NHCH.sub.2                                          CH.sub.2              "                          5-SO.sub.2 NHCH.sub.3)                                                                      "             "  CH.sub.2 CH.sub.2 SO.sub.2 N(CH.sub.3)CH.sub                                   .2 CH.sub.2 CH.sub. 2 "                          5-SO.sub.2 NHC.sub.2 H.sub.5                                                                "             "  CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6                                           H.sub.5)CH.sub.2 CH.sub.2                                                                            "                          5-SO.sub.2 NHC.sub.6 H.sub.11                                                               "             "  CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6                                           H.sub.11)CH.sub.2 CH.sub.2                                                                           "                          5-SO.sub.3 C.sub.6 H.sub.5                                                                  "             "  CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                            N(SO.sub.2 CH.sub.3)CH.sub.2 CH.sub.2                                                                "                          5-SO.sub.2 NHC.sub.6 H.sub.5                                                                "             "  CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6                                           H.sub.4-CH.sub.3)CH.sub.2 CH.sub.2                                                                   "                          5-NHCOCH.sub.3                                                                              "             "  CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6                                           H.sub.11)CH.sub.2 CH.sub.2                                                                           "                          5-SC.sub.2 H.sub.5                                                                          "             "  CH.sub.2 CH(Cl)CH.sub.2                                                                              "                          "            "             "  CH.sub.2 CH(OH)CH.sub.2                                                                              "                          "            "             "  CH.sub.2 CH(CH.sub.2 OCH.sub.3)                                                                      "                          "            "             "  CH.sub. 2 CH(CH.sub.2 OC.sub.6 H.sub.5)                                                              "                          "            "             "  CH.sub.2 CH(OCOCH.sub.3)CH.sub.2                                                                     "                          "            "             "  CH.sub.2 CH.sub.2 NHCOCH.sub.2                                                                       "                          "            "             "  CH.sub.2 CH.sub.2 CONHC.sub.2 H.sub.4                                                                "                          "            "             "  CH.sub.2 CH.sub.2 NHCOOCH.sub.2 CH.sub.2                                                             "                          "            "             "  CH.sub.2 CH.sub.2 COOCH.sub.2 CH.sub.2                                                               "                          "            "             "  CH.sub.2 CH.sub.2 NHCONHCH.sub.2 CH.sub.2                                                            "                          "            "             "  CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.sub.2                                        CH.sub.2              "                          "            "             "  CH.sub.2 CH.sub.2 N(COC.sub.6 H.sub.5)CH.sub                                   .2 CH.sub.2           "                          __________________________________________________________________________

                                      TABLE 4                                      __________________________________________________________________________      ##STR22##                                                                     R           (R.sub.1)m  R.sub.2         Z                  M                   __________________________________________________________________________     3-CH.sub.3  2-CH.sub.3  H               CH.sub.2 CH.sub.2  K.sup.+             "           2-Cl        "               "                  "                   "           2,5-di-Cl   "               "                  "                   "           2,5-di-CH.sub.3                                                                            "               "                  "                   "           2,5-di-OCH.sub.3                                                                           "               "                  "                   "           3-OCH.sub.3 C.sub.2 H.sub.5 "                  "                   "           2-OCH.sub.3, 5-NHCOCH.sub.3                                                                H               "                  "                   3-SCH.sub.3 2-CH.sub.3, 3-Cl                                                                           "               "                  "                   3-C.sub.6 H.sub.5                                                                          2-OCH.sub.3, 5-Cl                                                                          "               "                  "                   3-C.sub.6 H.sub.4p-Cl                                                                      3-NHCOCH.sub.3                                                                             C.sub.2 H.sub.5 "                  "                   3-C.sub.6 H.sub.4o-CN                                                                      3-NHCOC.sub.2 H.sub.5                                                                      C.sub.2 H.sub.4 OCH.sub.3                                                                      "                  "                   "           3-NHCOCH.sub.2 OH                                                                          CH.sub.2 C.sub.6 H.sub.5                                                                       "                  "                   "           3-NHCOCH.sub.2 OCH.sub.3                                                                   C.sub.6 H.sub.11                                                                               "                  "                   "           3-NHCOC.sub.6 H.sub.5                                                                      CH.sub.2 C.sub.6 H.sub.11                                                                      "                  "                   "           3-NHCOOC.sub.2 H.sub.5                                                                     CH.sub.2 CH.sub.2 OC.sub.6 H.sub.5                                                             "                  "                   "           3-NHCONHC.sub.2 H.sub.5                                                                    CH.sub.2 CH.sub.2 OH                                                                           "                  "                   "           3-NHCOC.sub.6 H.sub.11                                                                     CH.sub.2 CH(CH.sub.3).sub.2                                                                    "                  "                   3-C.sub.6 H.sub.5                                                                          3-NHCOCH.sub.2 CN                                                                          CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                            "                  "                   "           3-NHCOCH.sub.2 OC.sub.6 H.sub.5                                                            CH.sub.2 CH.sub.2 OCOCH.sub.3                                                                  "                  "                   "           3-NHCOCH.sub.2 C.sub.6 H.sub.5                                                             CH.sub.2 CH.sub.2 CONH.sub.2                                                                   "                  "                   "           3-CH.sub.3  CH.sub.2 CH.sub.2 NHCOCH.sub.3                                                                 "                  "                   "           "           CH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.3                                                          "                  "                   3-C.sub.6 H.sub.4p-CH.sub.2                                                                "           CH.sub.2 CH.sub.2 SO.sub.2 NH.sub.2                                                            "                  "                   3-C.sub.6 H.sub.5                                                                          "           CH.sub.2 CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.3                                                   "                  "                   "           "           CH.sub.2 CH.sub.2 SCH.sub.3                                                                    "                  "                   "           H                                                                                           ##STR23##      CH.sub.2 CH.sub.2 CH.sub.2                                                                        Na.sup.+            "           "                                                                                           ##STR24##      "                  "                   "           3-OC.sub.6 H.sub.5                                                                          ##STR25##      "                  NH.sub.4.sup.+      "           3-CH.sub.3  C.sub.6 H.sub.5  CH.sub.2 CH.sub.2 Na.sup.+            "           "                                                                                           ##STR26##      CH.sub.2 CH(CH.sub.2 OC.sub.6                                                  H.sub.5)           "                   3-SO.sub.2 CH.sub.3                                                                        "           CH.sub.2 CH.sub.2 COOCH.sub.3                                                                  CH.sub.2 CH(C.sub.6 H.sub.5)                                                                      "                   3-SCH.sub.2 CH.sub.2 COOCH.sub.3                                                           "           CH.sub.2 CH.sub.2 CN                                                                           CH.sub.2 CH(CH.sub.3)                                                                             "                   3-SCH.sub.2 C.sub.6 H.sub.5                                                                "           C.sub.2 H.sub.5 CH.sub.2 CH(OH)CH.sub.2                                                                           "                   3-SCH.sub.2 CH.sub.2 OCH.sub.3                                                             2-CH.sub.3 S                                                                               H               CH.sub.2 CH.sub.2 CH.sub.2                                                     CH.sub.2           "                   3-SC.sub.6 H.sub.11                                                                        3-CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OC.sub.2                                                      CH.sub.2 CH(OCOCH.sub.3)CH.sub.2                                                                  "                   3-SC.sub.2 H.sub.5                                                                         "           CH.sub.2 CH(OH)CH.sub.2 Cl                                                                     CH.sub.2 CH.sub.2  "                   "           2-OCH.sub.3, 5-CH.sub.3                                                                    C.sub.2 H.sub.5 "                  "                   "           "           H               CH.sub.2 CH.sub.2 OCH.sub.2                                                    CH.sub.2           "                   "           "           H               "                  "                   "           "           "               CH.sub.2 CH.sub.2 SO.sub.2                                                     CH.sub.2 CH.sub.2  K.sup.+             3-SCH.sub.2 COOCH.sub.3                                                                    3-CH.sub.3  C.sub.2 H.sub.5 CH.sub.2 CH.sub.2 SCH.sub.2                                                    CH.sub.2           "                   "           "           "               CH.sub.2 CH.sub.2 N(SO.sub.2                                                   CH.sub.3)CH.sub.2 CH.sub.2                                                                        "                   "           "           "               CH.sub.2 CH.sub.2 NHSO.sub.2                                                   CH.sub.2 CH.sub.2 CH.sub.2                                                     CH.sub.2           "                   "           "           "               CH.sub.2 CH.sub.2 SO.sub.2                                                     NHCH.sub.2 CH.sub.2                                                                               "                   3-SCH.sub.3 "           "               CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.                                             sub.2 CH.sub.2     "                   "           "           "               CH.sub.2 CH.sub.2 CONHC.sub.2                                                  H.sub.4            "                   "           "           "               CH.sub.2 CH.sub.2 NHCOCH.sub.2                                                                    "                   "           "           "               CH.sub.2 CH.sub.2 N(SO.sub. 2                                                  C.sub.6 H.sub.5)CH.sub.2 CH.sub.2                                                                 "                   3-SCH.sub.2 CH(CH.sub.3).sub.2                                                             "           "               CH.sub.2 CH.sub.2 SO.sub.2                                                     N(CH.sub.3)CH.sub.2 CH.sub.2                                                                      "                   "           "           "               CH.sub.2 CH.sub.2 SO.sub.2                                                     N(C.sub.6 H.sub.5)CH.sub.2                                                     CH.sub.2           "                   "           "           "               CH.sub.2 CH.sub.2 N(SO.sub.2                                                   C.sub.6 H.sub.11)CH.sub.2                                                                         "H.sub.2            "           "           "               CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.                                             sub.2 CH.sub.2     "                   "           "           "               CH.sub.2 CH(CH.sub.2 OCH.sub.3)                                                                   "                   "           "           "               CH.sub.2 CH(Cl)CH.sub.2                                                                           "                   "           "           "               CH.sub.2 CH.sub.2 NHCONHC.sub.2                                                H.sub.4            "                   "           "           "               CH.sub.2 CH.sub.2 NHCOOCH.sub.2                                                CH.sub.2           "                   "           "           "               CH.sub.2 CH.sub.2 COOCH.sub.2                                                  CH.sub.2           "                   __________________________________________________________________________

                                      TABLE 5                                      __________________________________________________________________________      ##STR27##                                                                     R             (R.sub.1)m   R.sub.3                                                                           R.sub.4                                                                              Z                M                         __________________________________________________________________________     3-CH.sub.3    H            CH.sub.3                                                                          CH.sub.3                                                                             CH.sub.2 CH.sub.2                                                                               K.sup.+                   "             7-CH.sub.3   "  "     "                "                         "             7-OCH.sub.3  "  "     "                "                         "             7-Cl         "  "     "                "                         "             5-CH.sub.3, 8-OCH.sub.3                                                                     "  "     "                "                         "             5,8-di-OCH.sub.3                                                                            "  "     "                "                         "             5,8-di-CH.sub.3                                                                             "  "     "                "                         "             5-Cl, 8-OCH.sub.3                                                                           "  "     "                "                         "             8-OCH.sub.3  "  "     "                "                         "             8-OC.sub.2 H.sub.5                                                                          H  H     "                "                         3-SCH.sub.3   7-CH.sub.3   "  "     "                "                         3-C.sub.6 H.sub.5                                                                            7-NHCOCH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                             "                Na.sup.+                  "             7-NHCOH      "  "     "                "                         "             7-NHCOCH.sub.2 OCH.sub.3                                                                    "  "     "                "                         "             7-NHCOCH.sub.2 OC.sub.6 H.sub.5                                                             H  CH(CH.sub.3).sub.2                                                                   "                "                         "             7-NHCOCH.sub.2 C.sub.6 H.sub.5                                                              "  "     "                "                         "             7-NHCOCH.sub.2 Cl                                                                           "  "     "                "                         "             7-NHCOC.sub.6 H.sub.5                                                                       "  "     "                "                         "             7-NHCOC.sub.6 H.sub.11                                                                      CH.sub.3                                                                          CH.sub.3                                                                             "                "                         "             7-NHCONHC.sub.2 H.sub.5                                                                     "  "     "                "                         "             7-NHSO.sub.2 CH.sub.3                                                                       "  "     "                "                         "             7-NHCOCH.sub.2 CN                                                                           "  "     "                "                         C.sub.6 H.sub.4o-CN                                                                          7-NHCOCH.sub.2 OH                                                                           "  "     "                "                         "             7-NHCOOC.sub.2 H.sub.5                                                                      "  "     CH.sub.2 CH.sub.2 CH.sub.2                                                                      "                                        ##STR28##   "  "     "                "                         "             8-OC.sub.4 H.sub.9n                                                                         H  CH.sub.3                                                                             CH.sub.2 CH.sub.2                                                                               "                         3-C.sub.6 H.sub.4p-CH.sub.3                                                                  7-CH.sub.3   CH.sub.3                                                                          H     "                "                         3-C.sub.6 H.sub.4o-Cl                                                                         ##STR29##   "  CH.sub.3                                                                             "                "                         3-SO.sub.2 CH.sub.3                                                                          7-OC.sub.2 H.sub.5                                                                          "  "     "                "                         3-SC.sub.6 H.sub.11                                                                          7-OC.sub.4 H.sub.9n                                                                         "  "     "                "                         3-SCH.sub.2 CH.sub.2 OCH.sub.3                                                               7-CH.sub.3   "  H     "                "                         3-SCH.sub.2 CH.sub.2 COOCH.sub.3                                                             "            "  "     "                "                         3-SCH.sub.2 C.sub.6 H.sub.5                                                                  "            "  "     CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                                             "                         3-CH.sub.2 CH.sub.3                                                                          "            "  "     CH.sub.2 CH.sub.2                                                                               "                         3-SCH.sub.2 COOCH.sub.3                                                                      "            "  "     "                "                         3-SCH.sub.2 CH.sub.2 COOC.sub.2 H.sub.5                                                      "            "  "     "                "                         3-SCH.sub.2 CH.sub.2 COOCH(CH.sub.3).sub.2                                                   "            "  "     CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2                                            CH.sub.2         K.sup.+                   3-SO.sub.2 C.sub.4 H.sub.9n                                                                  "            "  "     CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2                                                            "                         3-SCH.sub.2 CH.sub.2 CONHC.sub.4 H.sub.9n                                                    "            "  "     CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.2                                                            "                         3-SCH.sub.3   "            "  "     CH.sub.2 CH(C.sub.6 H.sub.5)                                                                    "                         "             "            "  "     CH.sub.2 CH(CH.sub.3)                                                                           "                         3-SC.sub.2 H.sub.5                                                                           "            "  "     CH.sub.2 CH(OH)CH.sub.2                                                                         "                         "             "            "  "     CH.sub.2 CH(Cl)CH.sub.2                                                                         "                         "             "            "  "     CH.sub.2 CH(CH.sub.2 OCH.sub.2                                                 CH.sub.3)        "                         "             "            "  "     CH.sub.2 CH(CH.sub.2 OC.sub.6                                                                   ".sub.5)                  "             "            "  "     CH.sub.2 CH.sub.2 N(SO.sub.2 CH.sub.3)                                         CH.sub.2 CH.sub.2                                                                               "                         "             "            "  "     CH.sub.2 CH.sub.2 CH.sub.2 NHSO.sub.2                                          CH.sub.2 CH.sub.2                                                                               "                         "             "            "  "     CH.sub.2 CH.sub.2 SO.sub.2 NHCH.sub.2                                          CH.sub.2         "                         "             "            "  "     CH.sub.2 CH.sub.2 NHCOCH.sub.2                                                                  "                         "             "            "  "     CH.sub.2 CH.sub.2 NHCOOCH.sub.2                                                CH.sub.2         "                         "             "            "  "     CH.sub.2 CH.sub.2 COOCH.sub.2                                                                   "H.sub.2                  "             "            "  "     CH.sub.2 CH.sub.2 CONHC.sub.2                                                                   ".sub.4                   "             "            "  "     CH.sub.2 CH.sub.2 NHCONHC.sub.2                                                H.sub.4          "                         "             "            "  "     CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6                                           H.sub.5)CH.sub.2 CH.sub.2                                                                       "                         "             "            "  "     CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.sub.                                         2 CH.sub.2       "                         "             "            "  "     CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6                                           H.sub.5)CH.sub.2 CH.sub.2                                                                       "                         "             "            "  "     CH.sub.2 CH.sub.2 SO.sub.2 N(CH.sub.3)                                         CH.sub.2 CH.sub.2                                                                               "                         __________________________________________________________________________

                                      TABLE 6                                      __________________________________________________________________________      ##STR30##                                                                     R             (R.sub.1)m    R.sub.3                                                                           Z                     M                         __________________________________________________________________________     3-CH.sub.3    6-CH.sub.3    H  CH.sub.2 CH.sub.2     K.sup.+                   "             H             H  "                     "                         "             "             CH.sub.3                                                                          "                     "                         "             6-CH.sub.3    "  "                     "                         H             "             "  CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                                                  "                         "             6-OCH.sub.3   "  "                     "                         3-SCH.sub.3   "             "  CH.sub.2 CH.sub.2     "                         3-CH.sub.2 CH.sub.3                                                                          6-CH.sub.3    "  CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2                                                                 "                         3-SCH.sub.2 CH.sub.2 OCH.sub.3                                                               "             "  CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2                                            CH.sub.2              "                         3-SCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                        "             "  CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.2                                                                 "                         3-SCH.sub.2 CH.sub.2 COOCH.sub.3                                                             "             "  CH.sub.2 CH(CH.sub.3) "                         3-SCH.sub.2 COOCH.sub.2 CH.sub.3                                                             "             "  CH.sub.2 CH(C.sub.6 H.sub.5)                                                                         "                         3-SCH.sub.2 C.sub.6 H.sub.5                                                                  6-OC.sub.2 H.sub.5                                                                           "  CH.sub.2 CH.sub.2     "                         3-SC.sub.6 H.sub.11                                                                          6-NHCOCH.sub.3                                                                               "  "                     Na.sup.+                  3-SCH.sub.3   6-NHCOH       "  "                     "                         "             6-NHCOCH.sub.2 CH.sub.2 OCH.sub.3                                                            "  "                     "                         "             6-NHCOCH.sub.2 Cl                                                                            "  "                     "                         "             6-NHCOCH.sub.2 CN                                                                            "  "                     "                         "             6-NHCOCH.sub.2 CONH.sub. 2                                                                   "  "                     "                         "             6-NHCOCH.sub.2 OC.sub.6 H.sub.5                                                              "  "                     "                         3-SO.sub.2 CH.sub.3                                                                          6-NHCOOC.sub.2 H.sub.5                                                                       "  "                     "                         3-SO.sub.2 C.sub.4 H.sub.9 n                                                                 6-NHCONHC.sub.2 H.sub.5                                                                      "  "                     "                         3-C.sub.6 H.sub.5                                                                            6-NHCOC.sub.6 H.sub.5                                                                        "  "                     "                         3-C.sub.6 H.sub.4o-CN                                                                        6-NHCOC.sub.6 H.sub.11                                                                       "  "                     "                         3-C.sub.6 H.sub.4o-Cl                                                                        6-NHSO.sub.2 CH.sub.3                                                                        "  "                     "                         3-C.sub.6 H.sub.4p-CH.sub.3                                                                  6-NHCOCH.sub.2 CH.sub.2 OCOCH.sub.3                                                          "  "                     "                         3-C.sub.6 H.sub.4m-CH.sub.3                                                                   ##STR31##    "  "                     "                         3-C.sub.6 H.sub.4o-CH.sub.3                                                                  6-NHCOCH.sub.2 CH.sub.2 CH.sub.2 OH                                                          "  "                     "                         3-C.sub.6 H.sub.4o-CONH.sub.2                                                                6-CH.sub.3    "  CH.sub.2 CH.sub.2 CH.sub.2                                                                           "                         3-C.sub.6 H.sub.4o-CN                                                                        "             "  CH.sub.2 CH.sub.2     "                         3-SCH.sub.2 CH.sub.2 OC.sub.6 H.sub.5                                                        "             "  "                     "                         3-SO.sub.2 C.sub.4 H.sub.9n                                                                  "             "  "                     "                         3-SO.sub.2 CH.sub.2 CH.sub.2 COOCH.sub.3                                                     "             "  "                     "                         3-SO.sub.2 CH.sub.2 COOCH.sub.3                                                              "             "  "                     "                         3-SO.sub.2 C.sub.6 H.sub.11                                                                  "             "  "                     "                         3-SO.sub.2 CH.sub.2 CH.sub.3                                                                 "             "  "                     "                         3-SO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                       "             H  CH.sub.2 CH(CH.sub.3) "                         3-SCH.sub.2 CH.sub.2 CONHC.sub.2 H.sub.4 OH                                                  "             CH.sub.3                                                                          CH.sub.2 CH.sub.2 N(SO.sub.2 CH.sub.3)CH.su                                    b.2 CH.sub.2          K.sup.+                   3-SCH.sub.2 CH.sub.3                                                                         "             "  CH.sub.2 CH.sub.2 SO.sub.2 NHCH.sub.2                                          CH.sub.2              "                         "             "             "  CH.sub.2 CH.sub.2 SO.sub.2 N(CH.sub.3)CH.su                                    b.2 CH.sub.2 CH.sub.2 "                         "             "             "  CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub. 6                                          H.sub.5)CH.sub.2 CH.sub.2                                                                            "                         "             "             "  CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6                                           H.sub.11)CH.sub.2 CH.sub.2                                                                           "                         "             "             "  CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                            N(SO.sub.2 CH.sub.3)CH.sub.2 CH.sub.2                                                                "                         "             "             "  CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6                                           H.sub.4p-CH.sub.3)CH.sub.2 CH.sub.2                                                                  "                         "             "             "  CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6                                           H.sub.11)CH.sub.2 CH.sub.2                                                                           "                         3-C.sub.6 H.sub.5                                                                            "             "  CH.sub.2 CH(Cl)CH.sub.2                                                                              "                         "             "             "  CH.sub.2 CH(OH)CH.sub.2                                                                              "                         "             "             "  CH.sub.2 CH(CH.sub.2 OCH.sub.3)                                                                      "                         "             "             "  CH.sub.2 CH(CH.sub.2 OC.sub.6 H.sub.5)                                                               "                         "             "             "  CH.sub.2 CH(OCOCH.sub.3)CH.sub.2                                                                     "                         "             "             "   CH.sub.2 CH.sub.2 NHCOCH.sub.2                                                                      "                         "             "             "  CH.sub.2 CH.sub.2 CONHC.sub.2 H.sub.4                                                                "                         "             "             "  CH.sub.2 CH.sub.2 NHCOOCH.sub.2 CH.sub.2                                                             "                         "             "             "  CH.sub.2 CH.sub.2 COOCH.sub.2 CH.sub.2                                                               "                         "             "             "  CH.sub.2 CH.sub.2 NHCONHCH.sub.2 CH.sub.2                                                            "                         "             "             "  CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.sub.2                                        CH.sub.2              "                         "             "             "  CH.sub.2 CH.sub.2 N(COC.sub.6 H.sub.5)CH.su                                    b.2 CH.sub.2          "                         __________________________________________________________________________

                                      TABLE 7                                      __________________________________________________________________________      ##STR32##                                                                     R              (R.sub.1)m R.sub.2        Z                 M                   __________________________________________________________________________     3-CH.sub.3, 4-Br                                                                              2-CH.sub.3 H              CH.sub.2 CH.sub.2 K.sup.+             "              2-Cl       "              "                 "                   "              2,5-di-Cl  "              "                 "                   "              2,5-di-CH.sub.3                                                                           "              "                 "                   "              2,5-di-OCH.sub.3                                                                          "              "                 "                   "              3-OCH.sub.3                                                                               C.sub.2 H.sub.5                                                                               "                 "                   "              2-OCH.sub.3, 5-NHCOCH.sub.3                                                               H              "                 "                   "              2-CH.sub.3, 3-Cl                                                                          "              "                 "                   "              2-OCH.sub.3, 5-Cl                                                                         "              "                 "                   "              3-NHCOCH.sub.3                                                                            C.sub.2 H.sub.5                                                                               "                 "                   "              3-NHCOC.sub.2 H.sub.5                                                                     C.sub.2 H.sub.4 OCH.sub.3                                                                     "                 "                   "              3-NHCOCH.sub.2 OH                                                                         CH.sub.2 C.sub.6 H.sub.5                                                                      "                 "                   H              3-NHCOCH.sub.2 OCH.sub.3                                                                  C.sub.6 H.sub.11                                                                              "                 "                   "              3-NHCOC.sub.6 H.sub.5                                                                     CH.sub.2 C.sub.6 H.sub.11                                                                     "                 "                   "              3-NHCOOC.sub.2 H.sub.5                                                                    CH.sub.2 CH.sub.2 OC.sub.6 H.sub.5                                                            "                 "                   3-CH.sub.34-Cl 3-NHCONHC.sub.2 H.sub.5                                                                   CH.sub.2 CH.sub.2 OH                                                                          "                 "                   "              3-NHCOC.sub.6 H.sub.11                                                                    CH.sub.2 CH(CH.sub.3).sub.2                                                                   "                 "                   "              3-NHCOCH.sub.2 CN                                                                         CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                           "                 "                   "              3-NHCOCH.sub.2 OC.sub.6 H.sub.5                                                           CH.sub.2 CH.sub.2 OCOCH.sub.3                                                                 "                 "                   3-CH.sub.34-CN 3-NHCOCH.sub.2 C.sub.6 H.sub.5                                                            CH.sub.2 CH.sub.2 CONH.sub.2                                                                  "                 "                   3-CH.sub.34-COOC.sub.2 H.sub.5                                                                3-CH.sub.3 CH.sub.2 CH.sub.2 NHCOCH.sub.3                                                                "                 "                   "              "          CH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.3                                                         "                 "                   "              "          CH.sub.2 CH.sub.2 SO.sub.2 NH.sub.2                                                           "                 "                   "              "          CH.sub.2 CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.3                                                  "                 "                   3-CH.sub.34-SCH.sub.2 CHCH.sub.2                                                              "          CH.sub.2 CH.sub.2 SCH.sub.3                                                                   "                 "                   "              H                                                                                          ##STR33##     CH.sub.2 CH.sub.2 CH.sub.2                                                                       Na.sup.+            "              "                                                                                          ##STR34##     "                 "                   3-CH.sub.34-SO.sub.2 C.sub.2 H.sub.5                                                          3-OC.sub.6 H.sub.5                                                                         ##STR35##     "                 NH.sub.4.sup.+      3-CH.sub.34-SC.sub.6 H.sub.11                                                                 3-CH.sub.3 C.sub.6 H.sub.5                                                                               CH.sub.2 CH.sub.                                                                                 Na.sup.+            3-CH.sub.34-OC.sub.2 H.sub.5                                                                  "                                                                                          ##STR36##     CH.sub.2 CH(CH.sub.2 OC.sub.6                                                  H.sub.5)          "                   3-Cl4-CN       "          CH.sub.2 CH.sub.2 COOCH.sub.3                                                                 CH.sub.2 CH(C.sub.6 H.sub.5)                                                                     "                   3-CH.sub.34-SCN                                                                               "          CH.sub.2 CH.sub.2 CN                                                                          CH.sub.2 CH(CH.sub.3)                                                                            "                   3-Br4-COOCH.sub.3                                                                             "          C.sub.2 H.sub.5                                                                               CH.sub.2 CH(OH)CH.sub.2                                                                          "                   3-CH.sub.34-COOC.sub.2 H.sub.5                                                                2-CH.sub.3 S                                                                              H              CH.sub.2 CH.sub.2 CH.sub.2                                                     CH.sub.2          "                   3-CH.sub.34-CONH.sub.2                                                                        3-CH.sub.3 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OC.sub.2                                      H.sub.5        CH.sub.2 CH(OCOCH.sub.3)CH.sub.2                                                                 "                   3-CH.sub.34-CONHC.sub.2 H.sub.4 OH                                                            "          CH.sub.2 CH(OH)CH.sub.2 Cl                                                                    CH.sub.2 CH.sub.2 "                   3-CH.sub.34-CONHC.sub.4 H.sub.9 -n                                                            2-OCH.sub.3, 5-CH.sub.3                                                                   C.sub.2 H.sub.5                                                                               "                 "                   3-CH.sub.34-OC.sub.6 H.sub.5                                                                  "          H              CH.sub.2 CH.sub.2 OCH.sub.2                                                    CH.sub.2          "                   3-CH.sub.34-OC.sub.6 H.sub.4p-CH.sub.3                                                        "          H              "                 "                   3-CH.sub.34-SC.sub.6 H.sub.5                                                                  "          "              CH.sub.2 CH.sub.2 SCH.sub.2                                                    CH.sub.2          K.sup.+             3-CH.sub.34-SCH.sub.2 CH.sub.2 OH                                                             3-CH.sub.3 C.sub.2 H.sub.5                                                                               CH.sub.2 CH.sub.2 SCH.sub.2                                                    CH.sub.2          "                   3-CH.sub.34-SCH.sub.2 CH.sub.3                                                                "          "              CH.sub.2 CH.sub.2 N(SO.sub.2                                                   CH.sub.3)CH.sub.2 CH.sub.2                                                                       "                    ##STR37##     "          "              CH.sub.2 CH.sub.2 NHSO.sub.2                                                   CH.sub.2 CH.sub.2 CH.sub.2                                                     CH.sub.2          "                   3-CH.sub.34-Br "          "              CH.sub.2 CH.sub.2 SO.sub.2                                                     NHCH.sub.2 CH.sub.2                                                                              "                   "              "          "              CH.sub.2 CH.sub.2 N(COCH.sub.3)CH                                              .sub.2 CH.sub.2   "                   "              "          "              CH.sub.2 CH.sub.2 CONHC.sub.2                                                  H.sub.4           "                   "              "          "              CH.sub.2 CH.sub.2 NHCOCH.sub.2                                                                   "                   "              "          "              CH.sub.2 CH.sub.2 N(SO.sub.2                                                   C.sub.6 H.sub.5)CH.sub.2                                                                         "H.sub.2            3-CH.sub.34-CONH.sub.2                                                                        "          "              CH.sub.2 CH.sub.2 SO.sub.2                                                     N(CH.sub.3)CH.sub.2 CH.sub.2                                                                     "                   3-CH.sub.34-CONHC.sub.3 H.sub.6 OCH.sub.3                                                     "          "              CH.sub.2 CH.sub.2 SO.sub.2                                                     N(C.sub.6 H.sub.5)CH.sub.2                                                     CH.sub.2          "                   3-CH.sub.34-Cl "          "              CH.sub.2 CH.sub.2 N(SO.sub.2                                                   C.sub.6 H.sub.11)CH.sub.2                                                      CH.sub.2          "                   "              "          "              CH.sub.2 CH.sub.2 N(COCH.sub.3)CH                                              .sub.2 CH.sub.2   "                   "              "          "              CH.sub.2 CH(CH.sub.2 OCH.sub.3)                                                                  "                   "              "          "              CH.sub.2 CH(Cl)CH.sub.2                                                                          "                   "              "          "              CH.sub.2 CH.sub.2 NHCONHC.sub.2                                                H.sub.4           "                   "              "          "              CH.sub.2 CH.sub.2 NHCOOCH.sub.2                                                CH.sub.2          "                   "              "          "              CH.sub.2 CH.sub.2 COOCH.sub.2                                                  CH.sub.2          "                   __________________________________________________________________________

                                      TABLE 8                                      __________________________________________________________________________      ##STR38##                                                                     R              (R.sub.1).sub.m                                                                            R.sub.3                                                                           R.sub.4                                                                              Z                M                         __________________________________________________________________________     3-CH.sub.34-Br H           CH.sub.3                                                                          CH.sub.3                                                                             CH.sub.2 CH.sub.2                                                                               K.sup.+                   "              7-CH.sub.3  "  "     "                "                         "              7-OCH.sub.3 "  "     "                "                         "              7-Cl        "  "     "                "                         "              5-CH.sub.3, 8-OCH.sub.3                                                                    "  "     "                "                         "              5,8-di-OCH.sub.3                                                                           "  "     "                "                         "              5,8-di-CH.sub.3                                                                            "  "     "                "                         "              5-Cl, 8-OCH.sub.3                                                                          "  "     "                "                         "              8-OCH.sub.3 "  "     "                "                         "              8-OC.sub.2 H.sub.5                                                                         H  H     "                "                         "              7-CH.sub.3  "  "     "                "                         3-CH.sub.34-CN 7-NHCOCH.sub.3                                                                             CH.sub.3                                                                          CH.sub.3                                                                             "                Na.sup.+                  "              7-NHCOH     "  "     "                "                         "              7-NHCOCH.sub.2 OCH.sub.3                                                                   "  "     "                "                         3-CH.sub.34-COOC.sub.2 H.sub.5                                                                7-NHCOCH.sub.2 OC.sub.6 H.sub.5                                                            H  CH(CH.sub.3).sub.2                                                                   "                "                         "              7-NHCOCH.sub.2 C.sub.6 H.sub.5                                                             "  "     "                "                         "              7-NHCOCH.sub.2 Cl                                                                          "  "     "                "                         3-CH.sub.3     7-NHCOC.sub.6 H.sub.5                                                                      "  "     "                "                         "              7-NHCOC.sub.6 H.sub.11                                                                     CH.sub.3                                                                          CH.sub.3                                                                             "                "                         3-CH.sub.34-Cl 7-NHCONHC.sub.2 H.sub.5                                                                    "  "     "                "                         "              7-NHCOCH.sub.2 CN                                                                          "  "     "                "                         "              7-NHCOCH.sub.2 OH                                                                          "  "     "                "                         3-Cl-4-CN      7-NHCOOC.sub.2 H.sub.5                                                                     "  "     CH.sub.2 CH.sub.2 CH.sub.2                                                                      "                         3-Br-4-COOCH.sub.3                                                                             ##STR39##  "  "     "                "                         34-SCH.sub.2 CH.sub.2 OCOCH.sub.3                                                             "           "  "     CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                                             "                         3-CH.sub.34-SCH.sub.3                                                                         "           "  "     CH.sub.2 CH.sub.2                                                                               "                         3-CH.sub.34-SO.sub.2 CH.sub.3                                                                 "           "  "     "                "                         3-CH.sub.34-SC.sub.6 H.sub.5                                                                  "           "  "     "                "                         3-CH.sub.34-SC.sub.6 H.sub.4p-C(CH.sub.3).sub.3                                               "           "  "     CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2                                            CH.sub.2         K.sup.+                   3-CH.sub.24-SC.sub.6 H.sub.4p-Cl                                                              "           "  "     CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2                                                            "                          ##STR40##     "           "  "     CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.2                                                            "                          ##STR41##     "           "  "     CH.sub.2 CH(C.sub.6 H.sub.5)                                                                    "                          ##STR42##     "           "  "     CH.sub.2 CH(CH.sub.3)                                                                           "                         3-CH.sub.34-SC.sub.6 H.sub.11                                                                 "           "  "     CH.sub.2 CH(OH)CH.sub.2                                                                         "                         3-CH.sub.34-SCN                                                                               "           "  "     CH.sub.2 CH(Cl)CH.sub.2                                                                         "                         3-CH.sub.34-OC.sub.6 H.sub.5                                                                  "           "  "     CH.sub.2 CH(CH.sub.2 OCH.sub.2                                                 CH.sub.3)        "                         3-CH.sub.34-OC.sub.2 H.sub.5                                                                  "           "  "     CH.sub.2 CH(CH.sub.2 OC.sub.6 H.sub.5)     3-CH.sub.34-SCH.sub.2 CHCH.sub.2                                                              "           "  "     CH.sub.2 CH.sub.2 N(SO.sub.2 CH.sub.3)                                         CH.sub.2 CH.sub.2                                                                               "                         3-CH.sub.34-Br "           "  "     CH.sub.2 CH.sub.2 CH.sub.2 NHSO.sub.2                                          CH.sub.2 CH.sub.2                                                                               "                         "              "           "  "     CH.sub.2 CH.sub.2 SO.sub.2 NHCH.sub.2                                          CH.sub.2                                   "              "           "  "     CH.sub.2 CH.sub.2 NHCOCH.sub.2                                                                  "                         "              "           "  "     CH.sub.2 CH.sub.2 NHCOOCH.sub.2                                                CH.sub.2         "                         "              "           "  "     CH.sub.2 CH.sub.2 COOCH.sub.2                                                                   "H.sub.2                  "              "           "  "     CH.sub.2 CH.sub.2 CONHC.sub.2                                                                   ".sub.4                   "              "           "  "     CH.sub.2 CH.sub.2 NHCONHC.sub.2                                                H.sub.4          "                         "              "           "  "     CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6                                           H.sub.5)CH.sub.2 CH.sub.2                                                                       "                         "              "           "  "     CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.sub.                                         2 CH.sub.2       "                         "              "           "  "     CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6                                           H.sub.5)CH.sub.2 CH.sub.2                                                                       "                         "              "           "  "     CH.sub. 2 CH.sub.2 SO.sub.2 N(CH.sub.3                                         )CH.sub.2 CH.sub.2                                                                              "                         __________________________________________________________________________

                                      TABLE 9                                      __________________________________________________________________________      ##STR43##                                                                     R                 (R.sub.1)m     R.sub.3                                                                            Z                      M                  __________________________________________________________________________     3-CH.sub.34-Cl    6-CH.sub.3     H   CH.sub.2 CH.sub.2      K.sup.+            "                 H              H   "                      "                  "                 "              CH.sub.3                                                                           "                      "                  "                 6-CH.sub.3     "   "                      "                  3-Cl4-CN          "              "   CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2       "                 6-OCH.sub.3    "   "                      "                  3-CH.sub.3        "              "   CH.sub.2 CH.sub.2      "                  3-CH.sub.34-COOC.sub.2 H.sub.5                                                                   6-CH.sub.3     "   CH.sub.2 CH.sub.2 OCH.sub. 2                                                                          "H.sub.2           3-CH.sub.34-CONH.sub.2                                                                           "              "   CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2                                            CH.sub.2               "                  3-CH.sub.34-CONHC.sub.2 H.sub.4 OH                                                               "              "   CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.2      3-CH.sub.34-CONHC.sub.4 H.sub.9n                                                                 "              "   CH.sub.2 CH(CH.sub.3)  "                  3-CH.sub.34-CONHC.sub.3 H.sub.6 OCH.sub.3                                                        "              "   CH.sub.2 CH(C.sub.6 H.sub.5)                                                                          "                  3-CH.sub.34-CO.sub.2 CH.sub.2 H.sub.2 OCH.sub.3                                                  6-OC.sub.2 H.sub.5                                                                            "   CH.sub.2 CH.sub.2      "                  3-CH.sub.34-CONHCH.sub.3                                                                         6-NHCOCH.sub.3 "   "                      Na.sup.+           3-CH.sub.34-Br    6-NHCOH        "   "                      "                  "                 6-NHCOCH.sub.2 CH.sub.2 OCH.sub.3                                                             "   "                      "                  "                 6-NHCOCH.sub.3 Cl                                                                             "   "                      "                  "                 6-NHCOCH.sub.2 CN                                                                             "   "                      "                  H                 6-NHCOCH.sub.2 CONH.sub.2                                                                     "   "                      "                  "                 6-NHCOCH.sub.2 OC.sub.6 H.sub.5                                                               "   "                      "                  3-CH.sub. 34-SC.sub.2 H.sub.5                                                                    6-NHCOOC.sub.2 H.sub.5                                                                        "   "                      "                  3-CH.sub.34-SCH.sub.2 CH.sub.2 OH                                                                6-NHCONHC.sub.2 H.sub.5                                                                       "   "                      "                  3-CH.sub.34-SCH.sub.2 CHCH.sub.2                                                                 6-NHCOC.sub.6 H.sub.5                                                                         "   "                      "                  3-CH.sub.34-SCH.sub.2 OCOCH.sub.3                                                                6-NHCOC.sub.6 H.sub.11                                                                        "   "                      "                  3-CH.sub.34-SC.sub.6 H.sub.5                                                                     6-NHSO.sub.2 CH.sub.3                                                                         "   "                      "                  3-CH.sub.34-SC.sub.6 H.sub.4p-C(CH.sub.3).sub.2                                                  6-NHCOCH.sub.2 CH.sub.2 OCOCH.sub.3                                                           "   "                      "                  3-CH.sub.34-SC.sub.6 H.sub.11                                                                     ##STR44##     "   "                      "                  3-CH.sub.34-SO.sub.2 CH.sub.2 CH.sub.2 OH                                                        6-NHCOCH.sub.2 CH.sub.2 CH.sub.2 OH                                                           "   "                      "                  3-CH.sub.34-SO.sub.2 CH.sub.2 CH.sub.3                                                           6-CH.sub.3     "   CH.sub.2 CH.sub.2 CH.sub.2                                                                            "                  3-CH.sub.34-OC.sub.6 H.sub.5                                                                     "              "   CH.sub.2 CH.sub.2      "                  3-CH.sub.34-OC.sub.6 H.sub.4p-OCH.sub.3                                                          "              "   "                      "                   ##STR45##        "              "   "                      "                   ##STR46##        "              "   "                      "                   ##STR47##        "              "   "                      "                  3-CH.sub.34-SCH.sub.2 CH(OH)CH.sub.2 OH                                                          "              "   "                      "                  3-CH.sub.34-SCH.sub.2 COOCH.sub.3                                                                "              "   "                      "                  3-CH.sub.34-OC.sub.2 H.sub.5                                                                     "              H   CH.sub.2 CH(CH.sub.3)  "                  3-CH.sub.34-Br    "              CH.sub.3                                                                           CH.sub.2 CH.sub.2 N(SO.sub.2                                                   CH.sub.3)CH.sub.2 CH.sub.2                                                                            K.sup.+            "                 "              "   CH.sub.2 CH.sub.2 SO.sub.2 NHCH.sub.2                                           CH.sub.2              "                  "                 "              "   CH.sub.2 CH.sub.2 SO.sub.2 N(CH.sub.3                                          )CH.sub.2 CH.sub.2 CH.sub.2                                                                           "                  "                 "              "   CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6                                           H.sub.5)CH.sub.2 CH.sub.2                                                                             "                  "                 "              "   CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6                                           H.sub.11)CH.sub.2 CH.sub.2                                                                            "                  "                 "              "   CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                            N(SO.sub.2 CH.sub.3)CH.sub.2                                                                          "H.sub.2           "                 "              "   CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6                                           H.sub.4p-CH.sub.3)CH.sub.2 CH.sub.2                                                                   "                  "                 "              "   CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6                                           H.sub.11)CH.sub.2 CH.sub.2                                                                            "                  "                 "              "   CH.sub.2 CH(Cl)CH.sub.2                                                                               "                  "                 "              "   CH.sub.2 CH(OH)CH.sub.2                                                                               "                  "                 "              "   CH.sub.2 CH(CH.sub.2 OCH.sub.3)                                                                       "                  "                 "              "   CH.sub.2 CH(CH.sub.2 OC.sub.6                                                  H.sub.5)               "                  "                 "              "   CH.sub.2 CH(OCOCH.sub.3)CH.sub.2                                                                      "                  "                 "              "   CH.sub.2 CH.sub.2 NHCOCH.sub.2                                                                        "                  "                 "              "   CH.sub.2 CH.sub.2 CONHC.sub.2                                                                         ".sub.4            "                 "              "   CH.sub.2 CH.sub.2 NHCOOCH.sub.2                                                CH.sub.2               "                  "                 "              "   CH.sub.2 CH.sub.2 COOCH.sub.2                                                  CH.sub.2               "                  "                 "              "   CH.sub.2 CH.sub.2 NHCONHCH.sub.2                                                                      "                  "                 "              "   CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.sub                                          .2 CH.sub.2            "                  "                 "              "   CH.sub.2 CH.sub.2 N(COC.sub.6                                                  H.sub.5)CH.sub.2 CH.sub.2                                                                             "                  __________________________________________________________________________

                                      TABLE 10                                     __________________________________________________________________________      ##STR48##                                                                     A       R          (R.sub.1)m                                                                               R.sub.2        Z              M                   __________________________________________________________________________     H       4-CN       2-CH.sub.3                                                                               H              CH.sub.2 CH.sub.2                                                                             K.sup.+             "       "          2-Cl      "              "              "                   "       "          2,5-di-Cl "              "              "                   "       "          2,5-di-CH.sub.3                                                                          "              "              "                   "       "          2,5-di-OCH.sub.3                                                                         "              "              "                   "       "          3-OCH.sub.3                                                                              C.sub.2 H.sub.5                                                                               "              "                   "       "          2-OCH.sub.3,                                                                             H              "              "                                      5-NHCOCH.sub.3                                              "       "          2-CH.sub.3, 3-Cl                                                                         "              "              "                   "       "          2-OCH.sub. 3, 5-Cl                                                                       "              "              "                   "       "          3-NHCOCH.sub.3                                                                           C.sub.2 H.sub.5                                                                               "              "                   "       "          3-NHCOC.sub.2 H.sub.5                                                                    C.sub.2 H.sub.4 OCH.sub.3                                                                     "              "                   "       H          3-NHCOCH.sub.2 OH                                                                        CH.sub.2 C.sub.6 H.sub.5                                                                      "              "                   "       "          3-NHCOCH.sub.2 OCH.sub.3                                                                 C.sub.6 H.sub.11                                                                              "              "                   "       "          3-NHCOC.sub.6 H.sub.5                                                                    CH.sub.2 C.sub.6 H.sub.11                                                                     "              "                   "       "          3-NHCOOC.sub.2 H.sub.5                                                                   CH.sub.2 CH.sub.2 OC.sub.6 H.sub.5                                                            "              "                   "       "          3-NHCONHC.sub.2 H.sub.5                                                                  CH.sub.2 CH.sub.2 OH                                                                          "              "                   C.sub.6 H.sub.5                                                                        3-SC.sub.2 H.sub.54-CN                                                                    3-NHCOC.sub.6 H.sub.11                                                                   CH.sub.2 CH(CH.sub.3).sub.2                                                                   "              "                   "       3-SC.sub.2 H.sub.54-COOCH.sub.3                                                           3-NHCOCH.sub.2 CN                                                                        CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                           "              "                   "       3-SC.sub.2 H.sub.54-CONH.sub.2                                                            3-NHCOCH.sub.2 OC.sub.6 H.sub.5                                                          CH.sub.2 CH.sub.2 OCOCH.sub.3                                                                 "              "                   "       3-SCH.sub.34-CN                                                                           3-NHCOCH.sub.2 C.sub.6 H.sub.5                                                           CH.sub.2 CH.sub.2 CONH.sub.2                                                                  "              "                   "       "          3-CH.sub.3                                                                               CH.sub.2 CH.sub.2 NHCOCH.sub.3                                                                "              "                   "       "          "         CH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.3                                                         "              "                   "       "          "         CH.sub.2 CH.sub.2 SO.sub.2 NH.sub.2                                                           "              "                   SO.sub.2 C.sub.6 H.sub.5                                                               "          "         CH.sub.2 CH.sub.2 cH.sub.2 SO.sub.2 CH.sub.3                                                  "              "                   COCH.sub.3                                                                             4-CN       "         CH.sub.2 CH.sub.2 SCH.sub.3                                                                   "              "                   H       "          H                                                                                         ##STR49##     CH.sub.2 CH.sub.2 CH.sub.2                                                                    Na.sup.+            "       "          "                                                                                         ##STR50##     "              "                   "       "          3-OC.sub.6 H.sub. 5                                                                       ##STR51##     "              NH.sub.4.sup.+      COOC.sub.2 H.sub.5                                                                     "          3-CH.sub.3                                                                               C.sub.6 H.sub.5                                                                               CH.sub.2 CH.sub.2                                                                             Na.sup.+            H       "          "                                                                                         ##STR52##     CH.sub.2 CH(CH.sub.2 OC.sub.6                                                  H.sub.5)       "                   CH.sub.3                                                                               4-CN       "         CH.sub.2 CH.sub.2 COOCH.sub.3                                                                 CH.sub.2 CH(C.sub.6 H.sub.5)                                                                  "                   "       4-COOCH.sub.3                                                                             "         CH.sub.2 CH.sub.2 CN                                                                          CH.sub.2 CH(CH.sub.3)              "       4-CONH.sub.2                                                                              "         C.sub.2 H.sub.5                                                                               CH.sub.2 CH(OH)CH.sub.2                                                                       "                   CH.sub.2 CH.sub.3                                                                      4-CN       2-CH.sub.3 S                                                                             H              CH.sub.2 CH.sub.2 CH.sub.2                                                     CH.sub.2       "                   C.sub.6 H.sub.5                                                                        "          3-CH.sub.3                                                                               C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OC.sub.2                                      H.sub.5        CH.sub.2 CH(OCOCH.sub.3)CH.sub                                                 .2             "                   "       4-COOCH.sub.3                                                                             "         CH.sub.2 CH(OH)CH.sub.2 Cl                                                                    CH.sub.2 CH.sub.2                                                                             "                   C.sub.6 H.sub.4p-Cl                                                                    "          2-OCH.sub.3, 5-CH.sub.3                                                                  C.sub.2 H.sub.5                                                                               "              "                   C.sub.6 H.sub.4o-CH.sub. 3                                                             "          "         H              CH.sub.2 CH.sub.2 OCH.sub.2                                                    CH.sub.2       "                   C.sub.6 H.sub.5                                                                        "          "         H              "              "                   "       "          "         "              CH.sub.2 CH.sub.2 SO.sub.2                                                     CH.sub.2 CH.sub.2                                                                             K.sup.+             H       4-CONHC.sub.2 H.sub.4 OH                                                                  3-CH.sub.3                                                                               C.sub.2 H.sub.5                                                                               CH.sub.2 CH.sub.2 SCH.sub.2                                                    CH.sub.2         "                 "       4-CONHC.sub.4 H.sub.9n                                                                    "         "              CH.sub.2 CH.sub.2 N(SO.sub.2                                                   CH.sub.3)CH.sub.2 CH.sub.2                                                                      "                 "       4-CONHC.sub.4 H.sub.9n                                                                    "         "              CH.sub.2 CH.sub.2 N(SO.sub.2                                                   CH.sub.3)CH.sub.2 CH.sub.2                                                                      "                 "       4-COOC.sub.2 H.sub.4 OCH.sub. 3                                                           "         "              CH.sub.2 CH.sub.2 NHSO.sub.2                                                   CH.sub.2 CH.sub.2 CH.sub.2                                                     CH.sub.2"                          "       4-CONHC.sub.3 H.sub.6 OCH.sub.3                                                           "         "              CH.sub.2 CH.sub.2 SO.sub.2                                                     NHCH.sub.2 CH.sub.2                                                                             "                 "       4-CN       "         "              CH.sub.2 CH.sub.2 N)COCH.sub.2                                                 )CH.sub.2 CH.sub.2                                                                              "-" " " " CH.                                                                  sub.2                                                                          CH.sub.2                                                                       CONHC.sub.2                                                                    H.sub.4 "         "       "          "         "              CH.sub.2 CH.sub.2 NHCOCH.sub.2                                                                  "                 "       "          "         "              CH.sub.2 CCH.sub.2 N(SO.sub.2                                                  C.sub.6 H.sub.5)CH.sub.2                                                       CH.sub.2         "                 SO.sub.2 CH.sub.3                                                                      4-CN       "         "              CH.sub.2 CH.sub.2 SO.sub.2                                                     N(CH.sub.3)CH.sub.2 CH.sub.2                                                                    "                 SO.sub.2 C.sub.6 H.sub.5                                                               "          "         "              CH.sub.2 CH.sub.2 SO.sub.2                                                     N(C.sub.6 H.sub.5)CH.sub.2                                                     CH.sub.2         "                 SO.sub.2 CH.sub.2 CH.sub.3                                                             "          "         "              CH.sub.2 CH.sub.2 N(SO.sub.2                                                   C.sub.6 H.sub.11)CH.sub.2                                                      CH.sub.2         "                 H       "          "         "              CH.sub.2 CH.sub.2 N(COCH.sub.3                                                 )CH.sub.2 CH.sub.2                                                                              "                 "       "          "         "              CH.sub.2 CH(CH.sub.2 OCH.sub.3                                                 )                "                 "       "          "         "              CH.sub.2 CH(Cl)CH.sub.2                                                                         "                 "       "          "         "              CH.sub.2 CH.sub.2 NHCONHC.sub.                                                 2 H.sub.4        "                 "       "          "         "              CH.sub.2 CH.sub.2 NHCOOCH.sub.                                                 2 CH.sub.2       "                 "       "          "         "              CH.sub.2 CH.sub.2 COOCH.sub.2                                                  CH.sub.2         "                 __________________________________________________________________________

                                      TABLE 11                                     __________________________________________________________________________      ##STR53##                                                                     A       R           (R.sub.1).sub.m                                                                             R.sub.3                                                                           R.sub.4                                                                              Z                 M                  __________________________________________________________________________     H       4-CN        H            CH.sub.3                                                                          CH.sub.3                                                                             CH.sub.2 CH.sub.2 K.sup.+            "       "           7-CH.sub.3   "  "     "                 "                  "       "           7-OCH.sub.3  "  "     "                 "                  "       "           7-Cl         "  "     "                 "                  "       "           5-CH.sub.3, 8-OCH.sub.3                                                                     "  "     "                 "                  "       "           5,8-di-OCH.sub.3                                                                            "  "     "                 "                  "       "           5,8-di-CH.sub.3                                                                             "  "     "                 "                  "       "           5-Cl, 8-OCH.sub.3                                                                           "  "     "                 "                  "       "           8-OCH.sub.3  "  "     "                 "                  "       "           8-OC.sub.2 H.sub.5                                                                          H  H     "                 "                  "       H           7-CH.sub.3   "  "     "                 "                  CH.sub.3                                                                               "           7-NHCOCH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                             "                 Na.sup.+           "       "           7-NHCOH      "  "     "                 "                  H       4-COOCH.sub.3                                                                              7-NHCOCH.sub.2 OCH.sub.3                                                                    "  "     "                 "                  H       4-COOC.sub.2 H.sub.5                                                                       7-NHCOCH.sub.2 OC.sub.6 H.sub.5                                                             H  CH(CH.sub.3).sub.2                                                                   "                 "                  H       4-COOC.sub.2 H.sub.4 OCH.sub.3                                                             7-NHCOCH.sub.2 C.sub.6 H.sub.5                                                              "  "     "                 "                  H       4-CONH.sub.2                                                                               7-NHCOCH.sub.2 Cl                                                                           "  "     "                 "                  H       4-CONHC.sub.2 H.sub.5                                                                      7-NHCOC.sub.6 H.sub.5                                                                       "  "     "                 "                  "       "           7-NHCOC.sub.6 H.sub. 11                                                                     CH.sub.3                                                                          CH.sub.3                                                                             "                 "                  "       "           7-NHCONHC.sub.2 H.sub.5                                                                     "  "     "                 "                  C.sub.6 H.sub.5                                                                        4-CN        7-NHSO.sub.2 CH.sub.3                                                                       "  "     "                 "                  "       "           7-NHCOCH.sub.2 CN                                                                           "  "     "                 "                  C.sub.6 H.sub.4p-Cl                                                                    "           7-NHCOCH.sub.2 OH                                                                           "  "     "                 "                  C.sub.6 H.sub.4p-CH.sub.3                                                              "           7-NHCOOC.sub.2 H.sub.5                                                                      "  "     CH.sub.2 CH.sub.2 CH.sub.2                                                                       "                  SO.sub.2 CH.sub.3                                                                      "                                                                                           ##STR54##   "  "     "                 "                  "       4-COOCH.sub.3                                                                              8-OC.sub.4 H.sub. 9n                                                                        H  CH.sub.3                                                                             CH.sub.2 CH.sub.2 "                  SO.sub.2 C.sub.6 H.sub.5                                                               "           7-CH.sub.3   CH.sub.3                                                                          H     "                 "                  "       4-CN                                                                                        ##STR55##   "  CH.sub.3                                                                             "                 "                  "       4-CONHC.sub.2 H.sub.4 OH                                                                   7-OC.sub. 2 H.sub.5                                                                         "  "     "                 "                  "       4-COOCH(CH.sub.3).sub.2                                                                    7-OC.sub.4 H.sub.9n                                                                         "  "     "                 "                  CH.sub.3                                                                               3-SC.sub.2 H.sub.54-CN                                                                     7-CH.sub.3   "  H     "                 "                  C.sub.6 H.sub.5                                                                        "           "            "  "     "                 "                  "       3-SC.sub.2 H.sub.54-COOCH.sub.3                                                            "            "  "     CH.sub.2 CH.sub.2 CH.sub.2                                                     CH.sub.2          "                  "       3-SCH.sub.34-COOC.sub.2 H.sub.5                                                            "            "  "     CH.sub.2 CH.sub.2 "                  "       3-SO.sub.2 CH.sub.34-COOCH.sub.3                                                           "            "  "     "                 "                  "       3-SC.sub.6 H.sub.54-COOCH.sub.3                                                            "            "  "     "                 "                  COCH.sub.3                                                                             4-CN        "            "  "     CH.sub.2 CH.sub.2 SO.sub.2                                                     CH.sub.2 CH.sub.2 K.sup.+            "       4-COOCH.sub.3                                                                              "            "  "     CH.sub.2 CH.sub.2 OCH.sub.2                                                    CH.sub.2          "                  CH.sub.2 CH.sub.2 OH                                                                   "           "            "  "     CH.sub.2 CH.sub.2 SCH.sub.2                                                    CH.sub.2          "                  H       3-CH.sub.2 CN4-CN                                                                          "            "  "     CH.sub.2 CH(C.sub.6 H.sub.5)                                                                     "                  H       3-CH.sub.2 CONH.sub.24-CN                                                                  "            "  "     CH.sub.2 CH(CH.sub.3)                                                                            "                  H       4-CN        "            "  "     CH.sub.2 CH(OH)CH.sub.2                                                                          "                  "       "           "            "  "     CH.sub.2 CH(Cl)CH.sub.2                                                                          "                  "       "           "            "  "     CH.sub.2 CH(CH.sub.2 OCH.sub.2                                                 CH.sub.3)         "                  "       "           "            "  "     CH.sub.2 CH(CH.sub.2 OC.sub.6                                                  H.sub.5)          "                  "       "           "            "  "     CH.sub.2 CH.sub.2 N(SO.sub.2                                                   CH.sub.3)CH.sub.2 CH.sub.2                                                                       "                  "       "           "            "  "     CH.sub.2 CH.sub.2 CH.sub.2                                                     NHSO.sub.2 CH.sub.2 CH.sub.2                                                                     "                  "       "           "            "  "     CH.sub.2 CH.sub.2 SO.sub.2                                                     NHCH.sub.2 CH.sub.                                                                               "                  "       "           "            "  "     CH.sub.2 CH.sub.2 NHCOCH.sub.3                                                                   "                  "       "           "            "  "     CH.sub.2 CH.sub.2 NHCOOCH.sub.2                                                CH.sub.2          "                  "       "           "            "  "     CH.sub.2 CH.sub.2 COOCH.sub.2                                                  CH.sub.2          "                  "       "           "            "  "     CH.sub.2 CH.sub.2 CONHC.sub.2                                                  H.sub.4           "                  "       "           "            "  "     CH.sub.2 CH.sub.2 NHCONHC.sub.2                                                H.sub.4           "                  "       "           "            "  "     CH.sub.2 CH.sub.2 N(SO.sub.2                                                   C.sub.6 H.sub.5)CH.sub.2                                                       CH.sub.2          "                  "       "           "            "  "     CH.sub.2 CH.sub.2 N(COCH.sub.3)C                                               H.sub.2 CH.sub.2  "                  "       "           "            "  "     CH.sub.2 CH.sub.2 SO.sub.2                                                     N(C.sub.6 H.sub.5)CH.sub.2                                                     CH.sub.2          "                  "       "           "            "  "     CH.sub.2 CH.sub.2 SO.sub.2                                                     N(CH.sub.3)CH.sub.2 CH.sub.2                                                                     "                  __________________________________________________________________________

                                      TABLE 12                                     __________________________________________________________________________      ##STR56##                                                                     A        R             (R.sub.1).sub.m                                                                              R.sub.3                                                                           Z                   M                  __________________________________________________________________________     H        4-CN          6-CH.sub.3    H  CH.sub.2 CH.sub.2   K.sup.+            "        "             H             H  "                   "                  CH.sub.3 "             "             CH.sub.3                                                                          "                   "                  "        4-COOCH.sub.3 6-CH.sub.3    "  "                   "                  "        4-COOC.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                        "             "  CH.sub.2 CH.sub.2 CH.sub.2                                                     CH.sub.2            "                  "        4-CONH.sub.2  6-OCH.sub.3   "  "                   "                  "        4-CONHC.sub. 2 H.sub.4 OH                                                                    "             "  CH.sub.2 CH.sub.2   "                  "        4-CONHC.sub.3 H.sub.6 OCH.sub.3                                                              6-CH.sub.3    "  CH.sub.2 CH.sub.2 OCH.sub.2                                                    CH.sub.2            "                  "        4-CONHC.sub.2 H.sub.4 NHCOCH.sub.3                                                           "             "  CH.sub.2 CH.sub.2 SO.sub.2                                                     CH.sub.2 CH.sub.2   "                  CH.sub.2 CH.sub.3                                                                       4-CN          "             "  CH.sub.2 CH.sub.2 SCH.sub.2                                                    CH.sub.2            "                  C.sub.6 H.sub.5                                                                         "             "             "  CH.sub.2 CH(CH.sub.3)                                                                              "                  "        4-COOCH.sub.2 CH.sub.3                                                                       "             "  CH.sub.2 CH(C.sub.6 H.sub.5)                                                                       "                  "        4-CONH.sub.2  6-OC.sub.2 H.sub.5                                                                           "  CH.sub.2 CH.sub.2   "                  C.sub.6 H.sub.4o-Cl                                                                     "             6-NHCOCH.sub.3                                                                               "  "                   Na.sup.+           H        "             6-NHCOH       "  "                   "                  "        4-COOCH.sub.3 6-NHCOCH.sub.2 CH.sub.2 OCH.sub.3                                                            "  "                   "                  "        "             6-NHCOCH.sub.2 Cl                                                                            "  "                   "                  "        4-CONHC.sub. 4 H.sub.9n                                                                      6-NHCOCH.sub.2 CN                                                                            "  "                   "                  "        "             6-NHCOCH.sub.2 CONH.sub.2                                                                    "  "                   "                  "        "             6-NHCOCH.sub.2 OC.sub.6 H.sub.5                                                              "  "                   "                  SO.sub.2 CH.sub.3                                                                       4-CN          6-NHCOOC.sub.2 H.sub.5                                                                       "  "                   "                  "        4-COOCH.sub.3 6-NHCONHC.sub.2 H.sub.5                                                                      "  "                   "                  H        3-CH.sub.2 CN4-CN                                                                            6-NHCOC.sub.6 H.sub.5                                                                        "  "                   "                  C.sub.6 H.sub.5                                                                         3-SCH.sub.34-CN                                                                              6-NHCOC.sub.6 H.sub.11                                                                       "  "                   "                  "        3-SCH.sub.2 CH.sub.34-CN                                                                     6-NHSO.sub.2 CH.sub.3                                                                        "  "                   "                  "        3-SCH.sub.2 CH.sub.34-COOCH.sub.3                                                            6-NHCOCH.sub.2 CH.sub.2 OCOCH.sub.3                                                          "  "                   "                  "        3-SCH.sub.34-CONHC.sub.4 H.sub.9n                                                             ##STR57##    "  "                   "                  SO.sub.2 C.sub.6 H.sub.5                                                                4-CN          6-NHCOCH.sub.2 CH.sub.2 CH.sub.2 OH                                                          "  "                   "                  "        4-COOCH.sub.3 6-CH.sub.3    "  CH.sub.2 CH.sub.2 CH.sub.2                                                                         "                  SO.sub.2 C.sub.6 H.sub.4p-CH.sub.3                                                      4-CN          "             "  CH.sub.2 CH.sub.2   "                  SO.sub.2 C.sub.4 H.sub.9n                                                               "             "             "  "                   "                  COCH.sub.3                                                                              "             "             "  "                   "                  COOC.sub.2 H.sub.5                                                                      "             "             "  "                   "                  CH.sub.2 CH.sub.2 OH                                                                    H             "             "  "                   "                  C.sub.6 H.sub.4o-CH.sub.3                                                               "             "             "  "                   "                  "        4-COOCH.sub.3 "             "  "                   "                  "        4-COOCH(CH.sub.3).sub.2                                                                      "             H  CH.sub.2 CH(CH.sub.3)                                                                              "                  SO.sub.2 C.sub.6 H.sub.11                                                               "             "             CH.sub.3                                                                          CH.sub.2 CH.sub.2 N(SO.sub.2                                                   CH.sub.3)CH.sub.2 CH.sub.2                                                                         K.sup.+            H        4-CN          "             "  CH.sub.2 CH.sub.2 SO.sub.2                                                     NHCH.sub.2 CH.sub.2 "                  "        "             "             "  CH.sub.2 CH.sub.2 SO.sub.2                                                     N(CH.sub.3 )CH.sub.2 CH.sub.2                                                  CH.sub.2            "                  "        "             "             "  CH.sub.2 CH.sub.2 SO.sub.2                                                     N(C.sub.6 H.sub.5)CH.sub.2                                                     CH.sub.2            "                  "        "             "             "  CH.sub.2 CH.sub.2 SO.sub.2                                                     N(C.sub.6 H.sub.11)CH.sub.2                                                    CH.sub.2            "                  "        "             "             "  CH.sub.2 CH.sub.2 CH.sub.2                                                     CH.sub.2 N(SO.sub.2 CH.sub.3)CH.su                                             b.2 CH.sub.2        "                  "        "             "             "  CH.sub.2 CH.sub.2 N(SO.sub.2                                                   C.sub.6 H.sub.4p-CH.sub.3)CH.sub.2                                              CH.sub.2 "                            "        "             "             "  CH.sub.2 CH.sub.2 N(SO.sub.2                                                   C.sub.6 H.sub.11)CH.sub.2                                                      CH.sub.2            "                  C.sub.6 H.sub.5                                                                         "             "             "  CH.sub.2 CH(Cl)CH.sub.2                                                                            "                  "        "             "             "  CH.sub.2 CH(OH)CH.sub.2                                                                            "                  "        "             "             "  CH.sub.2 CH(CH.sub.2 OCH.sub.3)                                                                    "                  "        "             "             "  CH.sub.2 CH(CH.sub.2 OC.sub.6                                                  H.sub.5)            "                  "        "             "             "  CH.sub.2 CH(OCOCH.sub.3)CH.sub.2                                                                   "                  "        "             "             "  CH.sub.2 CH.sub.2 NHCOCH.sub.2                                                                     "                  "        "             "             "  CH.sub.2 CH.sub.2 CONHC.sub.2                                                  H.sub.4             "                  "        "             "             "  CH.sub.2 CH.sub.2 NHCOOCH.sub.2                                                CH.sub.2            "                  "        "             "             "  CH.sub.2 CH.sub.2 COOCH.sub.2                                                  CH.sub.2            "                  "        "             "             "  CH.sub.2 CH.sub.2 NHCONHCH.sub.2                                               CH.sub.2            "                  "        "             "             "  CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.                                             sub.2 CH.sub.2      "                  "        "             "             "  CH.sub.2 CH.sub.2 N(COC.sub.6                                                  H.sub.5)CH.sub.2 CH.sub.2                                                                          "                  __________________________________________________________________________

    TABLE 13       ##STR58##          R   (R.sub.1).sub.m   R.sub.2       Z M                                   3,5-di-CN4-CH.sub.3 2-CH.sub.3 H      CH.sub.2       CH.sub.2 K.sup.+ " 2-Cl " " " " 2,5-di-Cl " " " " 2,5-di-CH.sub.3 " " "      3-CN5-C.sub.6 H.sub.5 2,5-di-OCH.sub.3 " " " 3-COOCH.sub.35-C.sub.6      H.sub.5 3-OCH.sub.3 C.sub.2 H.sub.5 " " 3-CONH.sub.25-C.sub.6 H.sub.5      2-OCH.sub.3, 5-NHCOCH.sub.3 H " " 3-CONHC.sub.2 H.sub.55-C.sub.6 H.sub.5      2-CH.sub.3, 3-Cl " " " 3-COOCH.sub.3 2-OCH.sub.3, 5-Cl " " " 3-CN      3-NHCOCH.sub.3 C.sub.2 H.sub.5 " " 3-CN4-CH.sub.35-COOC.sub.2 H.sub.5      3-NHCOC.sub.2 H.sub.5 C.sub.2 H.sub.4 OCH.sub.3 " " " 3-NHCOCH.sub.2 OH      CH.sub.2 C.sub.6 H.sub.5 " " H 3-NHCOCH.sub.2 OCH.sub.3 C.sub.6 H.sub.11      " " " 3-NHCOC.sub.6 H.sub.5 CH.sub.2 C.sub.6       H.sub.11 " " 3-CN4-CH.sub.35-COCH.sub.3 3-NHCOOC.sub.2 H.sub.5 CH.sub.2      CH.sub.2 OC.sub.6       H.sub.5 " " 3-COOCH.sub.34-CH.sub.35-CN 3-NHCONHC.sub.2 H.sub.5      CH.sub.2 CH.sub.2 OH " " 3-COOCH.sub.34-CH.sub.35-COC.sub.6 H.sub.5      3-NHCOC.sub.6 H.sub.11 CH.sub.2       CN(CH.sub.3).sub.2 " " 3-COOCH.sub.35-COC.sub.6 H.sub.5 3-NHCOCH.sub.2      CN CH.sub.2 CH.sub.2 CH.sub.2       CH.sub.3 " " 3-COOCH.sub.35-COCH(CH.sub.3).sub.2 3-NHCOCH.sub.2      OC.sub.6 H.sub.5 CH.sub.2 CH.sub.2 OCOCH.sub.3 " " " 3-NHCOCH.sub.2      C.sub.6 H.sub.5 CH.sub.2 CH.sub.2 CONH.sub.2 " " " 3-CH.sub.3 CH.sub.2      CH.sub.2 NHCOCH.sub.3 " " " " CH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.3 " "      " " CH.sub.2 CH.sub.2 SO.sub.2 NH.sub.2 " " " " CH.sub.2 CH.sub.2      CH.sub.2 SO.sub.2 CH.sub.3 " " 3-SO.sub.2 C.sub.6 H.sub.55-COCH.sub.3 "      CH.sub.2 CH.sub.2 SCH.sub.3 " " 3-SO.sub.2       CH.sub.35-CN H      ##STR59##       CH.sub.2 CH.sub.2 CH.sub.2 Na.sup.+ 3-SO.sub.2 C.sub.6 H.sub.55-Br "       ##STR60##       " " 3,5-di-SO.sub.2 CH.sub.3 3-OC.sub.6       H.sub.5      ##STR61##       " NH.sub.4.sup.+ 3,5-di-SO.sub.2 NH.sub.2 3-CH.sub.3 C.sub.6 H.sub.5      CH.sub.2 CH.sub.2 Na.sup.+ 3,5-di-SO.sub.2 N(C.sub.2 H.sub.5).sub.2 "       ##STR62##       CH.sub.2 CH(CH.sub.2 OC.sub.6 H.sub.5) " 3-CN5-COCH.sub.3 " CH.sub.2      CH.sub.2 COOCH.sub.3 CH.sub.2 CH(C.sub.6       H.sub.5) " 3-CN5-COCH(CH.sub.3).sub.2 " CH.sub.2 CH.sub.2 CN CH.sub.2      CH(CH.sub.3) " 3-CNSCOOC.sub.2 H.sub.5 " C.sub.2 H.sub.5 CH.sub.2      CH(OH)CH.sub.2 " 3-CONH.sub.25-COOC.sub.2 H.sub.5 2-CH.sub.3 S H      CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 " 3-CONH.sub.25-COCH(CH.sub.3).sub.2      3-CH.sub.3 C.sub.2 H.sub.4 OC.sub. 2 H.sub.4 OC.sub.2 H.sub.5 CH.sub.2      CH(OCOCH.sub.3)CH.sub.2 " 3-CONHC.sub.2 H.sub.4 OH5-COCH(CH.sub.3).sub.2      " CH.sub.2 CH(OH)CH.sub.2 Cl CH.sub.2       CH.sub.2 " " 2-OCH.sub.3, 5-CH.sub.3 C.sub.2 H.sub.5 " " " " H CH.sub.2      CH.sub.2 OCH.sub.2 CH.sub.2 " " " H " " " " " CH.sub.2 CH.sub.2 SO.sub.2      CH.sub.2 CH.sub.2 K.sup.+ 3-CONHC.sub.3 H.sub.6       OCH.sub.3SCOCH(CH.sub.3).sub.2 3-CH.sub.3 C.sub.2 H.sub.5 CH.sub.2      CH.sub.2 SCH.sub.2 CH.sub.2 " 3-CONHC.sub.4       H.sub.9n-5-COCH(CH.sub.3).sub.2 " " CH.sub.2 CH.sub.2 N(SO.sub.2      CH.sub.3)CH.sub.2 CH.sub.2 " 3-CONHC.sub.2 H.sub.4       OH5-COCH(CH.sub.3).sub.2 " " CH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.2      CH.sub.2 CH.sub.2 CH.sub.2 " 3-COOCH.sub.35-SO.sub.2 CH.sub.3 " "      CH.sub.2 CH.sub.2 SO.sub.2 NHCH.sub.2 CH.sub.2 " 3-CONHC.sub.2       H.sub.55-SO.sub.2 CH.sub.3 " " CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.sub.2      CH.sub.2 " 3-CONH.sub.25-SO.sub.2 CH.sub.3 " " CH.sub.2 CH.sub.2      CONHC.sub.2 H.sub.4 " 3-CONH.sub.25-SO.sub.2 C.sub.4 H.sub.9n " "      CH.sub.2 CH.sub.2 NHCOCH.sub.2 " 3-COOCH.sub.34-CH.sub.35-SCN " "      CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6 H.sub.5)CH.sub.2 CH.sub.2 "      3-CHO4-CH.sub.3 " " CH.sub.2 CH.sub.2 SO.sub.2 N(CH.sub.3)CH.sub.2      CH.sub.2 " 3-CONH.sub.25-C.sub.6 H.sub.4p-CH.sub.3 " " CH.sub.2 CH.sub.2      SO.sub.2 N(C.sub.6 H.sub.5)CH.sub.2 CH.sub.2 " 3-CN5-COOC.sub.2 H.sub.5      " " CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6 H.sub.11)CH.sub.2 CH.sub.2 "      3-COOCH.sub.35-COCH(CH.sub.3).sub.2 " " CH.sub.2 CH.sub.2       N(COCH.sub.3)CH.sub.2 CH.sub.2 " " " " CH.sub.2 CH(CH.sub.2 OCH.sub.3)      " " " " CH.sub.2 CH(Cl)CH.sub.2 " " " " CH.sub.2 CH.sub.2 NHCONHC.sub.2      H.sub.4 " " " " CH.sub.2 CH.sub.2 NHCOOCH.sub.2 CH.sub.2 " " " "      CH.sub.2 CH.sub.2 COOCH.sub.2       CH.sub.2 "

                                      TABLE 14                                     __________________________________________________________________________      ##STR63##                                                                        R                  (R.sub.1).sub.m                                                                           R.sub.3                                                                           R.sub.4                                                                                 Z              M                  __________________________________________________________________________     3-CONHC.sub.2 H.sub.55-COCH(CH.sub.3).sub.2                                                        H            CH.sub.3                                                                          CH.sub.3                                                                             CH.sub.2 CH.sub.2 K.sup.+            "                   7-CH.sub.3   "  "     "                 "                  3-CONH.sub.25-COCH(CH.sub.3).sub.2                                                                 7-OCH.sub.3  "  "     "                 "                  "                   7-Cl         "  "     "                 "                  "                   5-CH.sub.3, 8-OCH.sub.3                                                                     "  "     "                 "                  "                   5,8-di-OCH.sub.3                                                                            "  "     "                 "                  "                   5,8-di-CH.sub.3                                                                             "  "     "                 "                  "                   5-Cl, 8-OCH.sub.3                                                                           "  "     "                 "                  "                   8-OCH.sub.3  "  "     "                 "                  H                   8-OC.sub.2 H.sub.5                                                                          H  H     "                 "                  "                   7-CH.sub.3   "  "     "                 "                  3-COOCH.sub.35-COCH(CH.sub.3).sub.2                                                                7-NHCOCH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                             "                 Na.sup.+           "                   7-NHCOH      "  "     "                 "                  "                   7-NHCOCH.sub.2 OCH.sub.3                                                                    "  "     "                 "                  "                   7-NHCOCH.sub.2 OC.sub.6 H.sub.5                                                             H  CH(CH.sub.3).sub.2                                                                   "                 "                  "                   7-NHCOCH.sub.2 C.sub.6 H.sub.5                                                              "  "     "                 "                  3,5-di-CN4-CH.sub.3 7-NHCOCH.sub.2 Cl                                                                           "  "     "                 "                  "                   7-NHCOC.sub.6 H.sub.5                                                                       "  "     "                 "                  "                   7-NHCOC.sub.6 H.sub.11                                                                      CH.sub.3                                                                          CH.sub.3                                                                             "                 "                  "                   7-NHCONHC.sub.2 H.sub.5                                                                     "  "     "                 "                  "                   7-NHSO.sub.2 CH.sub.3                                                                       "  "     "                 "                  3-CONH.sub.25-C.sub.6 H.sub.5                                                                      7-NHCOCH.sub.2 CN                                                                           "  "     "                 "                  "                   7-NHCOCH.sub.2 OH                                                                           "  "     "                 "                  3-COOCH.sub.35-C.sub.6 H.sub.5                                                                     7-NHCOOC.sub.2 H.sub.5                                                                      "  "     CH.sub.2 CH.sub.2 CH.sub.2                                                                       "                  3-COOCH.sub.35-COCH.sub.3                                                                           ##STR64##   "  "     "                 "                  3-CN5-COOC.sub.2 H.sub.5                                                                           8-OC.sub.4 H.sub.9n                                                                         H  CH.sub.3                                                                             CH.sub.2 CH.sub.2 "                  3-CN4-CH.sub.35-COOC.sub.2 H.sub.5                                                                 7-CH.sub.3   CH.sub.3                                                                          H     "                 "                  3-CN4-CH.sub.35-COCH.sub.3                                                                          ##STR65##   "  CH.sub.3                                                                             "                 "                  3-COOCH.sub.34-CH.sub.35-CN                                                                        7-OC.sub.2 H.sub.5                                                                          "  "     "                 "                  3-CN4-CH.sub.35-CO.sub.2 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                        7-OC.sub.4 H.sub.9n                                                                         "  "     "                 "                  3-SO.sub.2 C.sub.6 H.sub.55-COCH.sub.3                                                             7-CH.sub.3   "  H     "                 "                  3-SO.sub.2 C.sub.6 H.sub.4p-Cl5-COCH.sub.3                                                         "            "  "     "                 "                  3-SO.sub.2 CH.sub.35-CN                                                                            "            "  "     CH.sub.2 CH.sub.2 CH.sub.2                                                     CH.sub.2          "                  3-COOCH.sub.35-Br   "            "  "     CH.sub.2 CH.sub.2 "                  3-COOCH.sub.35-SCN  "            "  "     "                 "                  3-CONHC.sub.2 H.sub.4 OH5-COCH(CH.sub.3).sub.2                                                     "            "  "     "                 "                  3-CONHC.sub.3 H.sub.6 OCH.sub.35-COCH(CH.sub.3).sub.2                                              "            "  "     CH.sub.2 CH.sub.2 SO.sub.2                                                     CH.sub.2 CH.sub.2 K.sup.+            3-CN5-SO.sub.2 CH.sub.3                                                                            "            "  "     CH.sub.2 CH.sub.2 OCH.sub.2                                                    CH.sub.2          "                  3,5-di-SO.sub.2 NH.sub.2                                                                           "            "  "     CH.sub.2 CH.sub.2 SCH.sub.2                                                    CH.sub.2          "                  3,5-di-SO.sub.2 NHC.sub.2 H.sub.5                                                                  "            "  "     CH.sub.2 CH(C.sub.6 H.sub.                                                                       ")                 3-COOCH.sub.35-COC.sub.6 H.sub.5                                                                   "            "  "     CH.sub.2 CH(CH.sub.3)                                                                            "                  3-CONHC.sub.4 H.sub.9n-5-COC.sub.6 H.sub.5                                                         "            "  "     CH.sub.2 CH(OH)CH.sub.2                                                                          "                  3-COOCH.sub.35-SO.sub.2 CH.sub.3                                                                   "            "  "     CH.sub.2 CH(Cl)CH.sub.2                                                                          "                  3-CONHC.sub.2 H.sub.4 OH5-SO.sub.2 CH.sub.3                                                        "            "  "     CH.sub.2 CH(CH.sub.2 OCH.sub.2                                                 CH.sub.3)         "                  3-CHO               "            "  "     CH.sub.2 CH(CH.sub.2 OC.sub.6                                                  H.sub.5)          "                  3-SO.sub.2 C.sub.6 H.sub.5                                                                         "            "  "     CH.sub.2 CH.sub.2 N(SO.sub.2                                                   CH.sub.3)CH.sub.2 CH.sub.2                                                                       "                  3-CONHC.sub.2 H.sub.55-COCH(CH.sub.3).sub.2                                                        "            "  "     CH.sub.2 CH.sub.2 CH.sub.2                                                     NHSO.sub.2 CH.sub.2 CH.sub.2                                                                     "                  "                   "            "  "     CH.sub.2 CH.sub.2 SO.sub.2                                                     NHCH.sub.2 CH.sub.2                                                                              "                  "                   "            "  "     CH.sub.2 CH.sub.2 NHCOCH.sub.2                                                                   "                  "                   "            "  "     CH.sub.2 CH.sub.2 NHCOOCH.sub.2                                                CH.sub.2          "                  "                   "            "  "     CH.sub.2 CH.sub.2 COOCH.sub.2                                                  CH.sub.2          "                  "                   "            "  "     CH.sub.2 CH.sub.2 CONHC.sub.2                                                  H.sub.4           "                  "                   "            "  "     CH.sub.2 CH.sub.2 NHCONHC.sub.2                                                H.sub.4           "                  "                   "            "  "     CH.sub.2 CH.sub.2 N(SO.sub.2                                                   C.sub.6 H.sub.5)CH.sub.2                                                       CH.sub.2          "                  "                   "            "  "     CH.sub.2 CH.sub.2 N(COCH.sub.3)C                                               H.sub.2 CH.sub.2  "                  3-COOCH.sub.34-CH.sub.35-CONH.sub.2                                                                "            "  "     CH.sub.2 CH.sub.2 SO.sub.2                                                     N(C.sub.6 H.sub.5)CH.sub.2                                                     CH.sub.2          "                  "                   "            "  "     CH.sub.2 CH.sub.2 SO.sub.2                                                     N(CH.sub.3)CH.sub.2 CH.sub.2                                                                     "                  __________________________________________________________________________

                                      TABLE 15                                     __________________________________________________________________________      ##STR66##                                                                     R                   (R.sub.1).sub.m                                                                              R.sub.3                                                                           Z                      M                  __________________________________________________________________________     3-COOCH.sub.35-COCH(CH.sub.3).sub.2                                                                6-CH.sub.3    H  CH.sub.2 CH.sub.2      K.sup.+            3-CONH.sub.25-COCH(CH.sub.3).sub.2                                                                 H             H  "                      "                  3-CN5-COCH(CH.sub.3).sub.2                                                                         "             CH.sub.3                                                                          "                      "                  "                   6-CH.sub.3    "  "                      "                  3-CONH.sub.25-C.sub.6 H.sub.5                                                                      "             "  CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                                                   "                  "                   6-OCH.sub.3   "  "                      "                  "                   "             "  CH.sub.2 CH.sub.2      "                  3-CN5-C.sub. 6 H.sub.5                                                                             6-CH.sub.3    "  CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2                                                                  "                  3-CONHC.sub.2 H.sub.4 OH5-C.sub.6 H.sub.5                                                          "             "  CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2                                            CH.sub.2               "                  3-CONHC.sub.2 H.sub.55-COC.sub.6 H.sub.5                                                           "             "  CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.2                                                                  "                  3-CONHCH.sub.35-COC.sub.6 H.sub.5                                                                  "             "  CH.sub.2 CH(CH.sub.3)  "                  3-CN4-CH.sub.35-COOC.sub.2 H.sub.5                                                                 "             "  CH.sub.2 CH(C.sub.6 H.sub.5)                                                                          "                  3-CN4-CH.sub.35-COOC.sub.2 H.sub.4 OCH.sub.3                                                       6-OC.sub.2 H.sub.5                                                                           "  CH.sub.2 CH.sub.2      "                  3-CHO4,5-di-CH.sub.3                                                                               6-NHCOCH.sub.3                                                                               "  "                      Na.sup.+           3-CN4-CH.sub.35-SCH.sub.3                                                                          6-NHCOH       "  "                      "                  3-COOCH.sub.34-CH.sub.35-CONH.sub.2                                                                6-NHCOCH.sub.2 CH.sub.2 OCH.sub.3                                                            "  "                      "                  3-CONH.sub.24-CH.sub.35-CN                                                                         6-NHCOCH.sub.2 Cl                                                                            "  "                      "                  3,5-di-CN4-CH.sub.3 6-NHCOCH.sub.2 CN                                                                            "  "                      "                  "                   6-NHCOCH.sub.2 CONH.sub.2                                                                    "  "                      "                  H                   6-NHCOCH.sub.2 OC.sub.6 H.sub.5                                                              "  "                      "                  "                   6-NHCOOC.sub.2 H.sub.5                                                                       "  "                      "                  3-CONH.sub.24-CH.sub.35-COOCH.sub.3                                                                6-NHCONHC.sub.2 H.sub.5                                                                      "  "                      "                  3-SO.sub.2 CH.sub.35-COCH.sub.3                                                                    6-NHCOC.sub.6 H.sub.5                                                                        "  "                      "                  3-SO.sub.2 C.sub.6 H.sub.55-COCH.sub.3                                                             6-NHCOC.sub.6 H.sub.11                                                                       "  "                      "                  3-SO.sub.2 C.sub.6 H.sub.4p-Cl5-COCH.sub.3                                                         6-NHSO.sub.2 CH.sub.3                                                                        "  "                      "                  3-SO.sub.2 CH.sub.35-Br                                                                            6-NHCOCH.sub.2 CH.sub.2 OCOCH.sub.3                                                          "  "                      "                  3,5-di-SO.sub.2 CH.sub.3                                                                            ##STR67##    "  "                      "                  3,5-di-SO.sub.2 NH.sub.2                                                                           6-NHCOCH.sub.2 CH.sub.2 CH.sub.2 OH                                                          "  "                      "                  3,5-di-SO.sub.2 NHC.sub.2 H.sub.5                                                                  6-CH.sub.3    "  CH.sub.2 CH.sub.2 CH.sub.2                                                                            "                  3-CONHC.sub.2 H.sub.4 OH5-COCH(CH.sub.3).sub.2                                                     "             "  CH.sub.2 CH.sub.2      "                  3-CONHC.sub.3 H.sub.6 OCH.sub.35-COCH(CH.sub.3).sub.2                                              "             "  "                      "                  3-CONHC.sub.2 H.sub.4 NHCOCH.sub.3                                                                 "             "  "                      "                  3-CONHC.sub.4 H.sub.9n-5-C.sub.6 H.sub.5                                                           "             "  "                      "                  3-CN5-COOC.sub.2 H.sub.5                                                                           "             "  "                      "                  3-CN4-CH.sub.35-COOCH(CH.sub.3).sub.2                                                              "             "  "                      "                  3-CN4-CH.sub.35-CONHC.sub.2 H.sub.5                                                                "             "  "                      "                  3-CN4-CH.sub.35-CONHC.sub.6 H.sub.5                                                                "             H  CH.sub.2 CH(CH.sub.3)  "                  3-CONH.sub.25-SO.sub.2 CH.sub.3                                                                    "             CH.sub.3                                                                          CH.sub.2 CH.sub.2 N(SO.sub.2                                                   CH.sub.3)CH.sub.2 CH.sub.2                                                                            K.sup.+            3-CONH.sub.25-COCH(CH.sub.3).sub.2                                                                 "             "  CH.sub.2 CH.sub.2 SO.sub.2 NHCH.sub.2                                           CH.sub.2              "                  "                   "             "  CH.sub.2 CH.sub.2 SO.sub.2 N(CH.sub.3                                          )CH.sub.2 CH.sub.2 CH.sub.2                                                                           "                  "                   "             "  CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6                                           H.sub.5)CH.sub.2 CH.sub.2                                                                             "                  "                   "             "  CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6                                           H.sub.11)CH.sub.2 CH.sub.2                                                                            "                  "                   "             "  CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                            N(SO.sub.2 CH.sub.3)CH.sub.2                                                                          "H.sub.2           "                   "             "  CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6                                           H.sub.4p-CH.sub.3)CH.sub.2 CH.sub.2                                                                   "                  3-CONHC.sub.2 H.sub.55-COCH(CH.sub.3).sub.2                                                        "             "  CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6                                           H.sub.11)CH.sub.2 CH.sub.2                                                                            "                  "                   "             "  CH.sub.2 CH(Cl)CH.sub.2                                                                               "                  "                   "             "  CH.sub.2 CH(OH)CH.sub.2                                                                               "                  "                   "             "  CH.sub.2 CH(CH.sub.2 OCH.sub.3)                                                                       "                  "                   "             "  CH.sub.2 CH(CH.sub.2 OC.sub.6                                                  H.sub.5)               "                  "                   "             "  CH.sub.2 CH(OCOCH.sub.3                                                                               "CH.sub.2          "                   "             "  CH.sub.2 CH.sub.2 NHCOCH.sub.2                                                                        "                  "                   "             "  CH.sub.2 CH.sub.2 CONHC.sub.2                                                                         ".sub.4            "                   "             "  CH.sub.2 CH.sub.2 NHCOOCH.sub.2                                                CH.sub.2               "                  "                   "             "  CH.sub.2 CH.sub.2 COOCH.sub.2                                                  CH.sub.2               "                  "                   "             "  CH.sub.2 CH.sub.2 NHCONHCH.sub.2                                               CH.sub.2               "                  "                   "             "  CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.sub                                          .2 CH.sub.2            "                  "                   "             "  CH.sub.2 CH.sub.2 N(COC.sub.6                                                  H.sub.5)CH.sub.2 CH.sub.2                                                                             "                  __________________________________________________________________________

The invention has been described in detail with particular reference to preferred embodiments thereof, but it will be understood that variations and modifications can be effected within the spirit and scope of the invention. 

We claim:
 1. A compound of the formulae D-N═N-Coupler, wherein D is selected from the heterocyclic amines of the formulae ##STR68## wherein ring A is unsubstituted or substituted with a group selected from alkyl, alkoxy, halogen, alkylsulfonyl, SO₂ -aryl, SO₂ NH₂, SO₂ NH-alkyl, SO₂ N-(dialkyl), alkanoylamino, aryl, arylthio, alkenylthio, cyclohexylthio, thiocyano, cyclohexylsulfonyl, alkylthio, and cyclohexyl;ring B is unsubstituted or substituted with a group selected from alkyl, aryl, alkylthio, cyclohexylthio and alkylsulfonyl; ring C is unsubstituted or substituted with one or two groups selected from alkyl, halogen, cyano, carbamoyl, CONH-alkyl, alkoxycarbonyl, alkylthio, alkenylthio, arylthio, cyclohexylthio, aryloxy, and alkoxy; ring D is unsubstituted or substituted with one or two groups selected from alkyl, alkoxycarbonyl, alkylthio, aryl, cyano, carbamoyl, alkyl carbamoyl, alkylcarbonyl and alkyl sulfonyl; and the A group on the 1-nitrogen of ring D is hydrogen, alkyl, alkoxycarbonyl, aryl, alkylsulfonyl, arylsulfonyl, or alkanoyl; ring E is unsubstituted or substituted with one to three groups selected from alkyl, cyano, alkoxycarbonyl, alkanoyl, aroyl, alkylsulfonyl, arylsulfonyl, carbamoyl, alkyl carbamoyl, aryl, halogen, sulfamoyl, and formyl; wherein the various alkyl or alkylene portions of the above groups are unsubstituted or substituted with one to three groups selected from hydroxy, halogen, alkoxy, aryl, aryloxy, cyclohexyl, alkylcyclohexyl, acyloxy, alkoxy carbonyl, acylamido, alkylsulfonamido, succinimido, glutarimido, phthalimido, 2-pyrrolidono, cyano, carbamoyl, alkoxyalkoxy, alkylthio, halogen, arylthio, alkylsulfonyl and arylsulfonyl; and wherein the various above aryl groups are unsubstituted or substituted with one to three groups selected from alkyl, alkoxy, halogen, alkoxy carbonyl, alkyl sulfonyl, and alkylthio; and the Coupler is selected from those of the formulae ##STR69## wherein R₁ is selected from hydrogen; alkyl; halogen; alkoxy; aryloxy; --NHCO--R₅ ; --NHSO₂ --R₅ ; wherein R₅ is selected from alkyl and alkyl substituted with hydroxy, alkoxy, cyano, aryloxy, aryl, halogen, cycloalkyl, alkyl carbonyloxy, or carbamoyl; aryl; alkylamine; and 2-furyl; R₂ is selected from hydrogen; aryl; cycloalkyl; alkyl and alkyl substituted with alkoxy, alkoxyalkoxy, hydrogen, aryloxy, aryl, cycloalkyl, alkylcycloalkyl, furyl, NHCOR₅, NHSO₂ R₅, aryloxy, carbamoyl, alkyl carbamoyl, cyano, alkanoyloxy, halogen, alkoxycarbonyl, succinimido, glutarimido, phthalimido, 2-pyrrolidono, sulfamoyl, alkyl substituted sulfamoyl, alkylsulfonamido, NHSO₂ -aryl, NHCOO-alkyl, NHCONH-alkyl, formamido, alkylsulfonyl, arylsulfonyl, alkylthio, arylthio, or SO₃ M; n is 0, 1 or 2; M is Na⁺, K⁺, NH₄ ⁺, or H⁺ ; R₃ and R₄ are each selected from hydrogen or alkyl; Z is selected from straight or branched chain alkylene; alkylene substituted with aryl, aryloxy, alkoxy, halogen, aryloxy or SO₃ M; --CH₂ (CH₂)_(m) --X--CH₂ (CH₂)_(p), where m is 1, 2, or 3, p is 0, 1, 2, or 3, and X is O, S, SO₂, --SO₂ NH--, ##STR70## and the various aryl groups on the couplers are unsubstituted or substituted with alkyl, alkoxy, or halogen.
 2. A compound according to claim 1 wherein R₁ is selected from hydrogen, alkyl, and alkoxy; R₂ is selected from hydrogen and alkyl; and Z is straight or branched chain alkylene.
 3. A compound according to claim 1 having the formula ##STR71##
 4. A compound according to claim 1 having the formula ##STR72##
 5. A compound according to claim 1 having the formula ##STR73##
 6. A compound according to claim 1 having the formula ##STR74##
 7. A compound according to claim 1 having the formula ##STR75##
 8. A compound according to claim 1 having the formula ##STR76##
 9. A compound according to claim 1 having the formula ##STR77##
 10. A compound according to claim 1 having the formula ##STR78##
 11. A compound according to claim 1 having the formula ##STR79## 